Category: 14248-66-9

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Titanium(0) reagents. III. A convenient preparation of 4-pyridinamine derivatives》. Authors are Malinowski, Marek; Kaczmarek, Lukasz.The article about the compound:3,5-Dimethyl-4-nitropyridine 1-oxidecas:14248-66-9,SMILESS:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]).Application In Synthesis of 3,5-Dimethyl-4-nitropyridine 1-oxide. Through the article, more information about this compound (cas:14248-66-9) is conveyed.

Ti(0) slurry, easily accessible by the reduction of TiCl4 with LiAlH4 or Mg in THF, is an excellent reagent for the reduction of N-nitropyridine N-oxides, e.g., I (R = H, Me, F, Cl) to 4-aminopyridines, e.g., II. The reaction proceeds smoothly and fast at room temperature giving the amines in >90% yields.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzoylacetamide and iminobenzoylacetamide》. Authors are Checchi, Silvio; Papini, Piero.The article about the compound:3,5-Dimethyl-4-nitropyridine 1-oxidecas:14248-66-9,SMILESS:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]).Electric Literature of C7H8N2O3. Through the article, more information about this compound (cas:14248-66-9) is conveyed.

cf. CA 53, 21974b. BzCH2CN (I) was prepared in excellent yields from BzCH2CONH2 (II) and POCl3. Similar treatment of PhC(:NH)CH2CN (III) gave 6,3,2,4-Cl(CN)Ph2C5HN (IV), converted to give various 3,6-disubstituted 2,4-diphenylpyridines, N:CPh:CR:CPh.CH:CR’ (V). II (10 g.) and 18 g. POCl3 heated (H2O-free atm.) 30 min. on a steam bath at 60-70°, the cooled mixture decomposed with cold H2O, and the solid isolated and recrystallized repeatedly from H2O gave crystalline I, m. 70-2°. III (5 g.) and 8 g. POCl3 similarly heated 1 hr. at 70-80°, the cooled mass taken up in cold H2O, the washed (H2O, alc., Et2O) and dried product taken up in alc. containing a trace of HCl, and the crystalline material recrystallized from alc. yielded IV, m. 178-80°. IV (2 g.) refluxed 1 hr. in alc. containing 1 g. KOH and concentrated, the solution neutralized with dilute HCl, and the precipitate recrystallized from alc. gave V (R = CN, R’ = OH), m. 150°. IV (2 g.) heated 4 hrs. at 180° in a sealed tube with excess alc. NH3, the cooled mixture evaporated, and the product separated and recrystallized from ClCH:CCl2 yielded V (R = CN, R’ = NH2) hemihydrate, m. 214-15°. IV (5 g.) refluxed in alc. with powd. Zn, the filtered solution evaporated on a steam bath, and the residue taken up in a min. of HCONMe2 and diluted with H2O gave V(R = CN, R’ = H) (VI), m. 175-7° (alc.). VI (3 g.) heated 6 hrs. at 180-200° with concentrated HCl in a sealed tube, the liquid poured into hot H2O, the filtered solution neutralized with NH4OH, and the precipitate crystallized from alc. gave V(R = CO2H, R’ = H), m. 248-50°, decarboxylated by heating at 250° to V (R = R’ = H), characterized as the sulfate, m. 245° (darkening), and as the picrate, m. 187° (decomposition). IV (3 g.) refluxed 7 hrs. in 40% alc. KOH, the solvent evaporated, and the residue taken up in H2O and acidified with dilute HCl gave V (R = CONH2, R’ = OH), m. 287-9° (alc.), converted by heating 6 hrs. in a sealed tube at 180-90° with concentrated HCl to give V (R = H, R’ = OH), m. 210° (alc.) (also obtained similarly from IV); picrate m. 193-5° (alc.). VI (1 g.) boiled 2-3 min. in 4 ml. dilute H2SO4, the mixture boiled with addition of H2O, the cooled filtered solution made alk. with dilute NH4OH, and the precipitate crystallized from AcOEt and CHCl3 gave V (R = CONH2, R’ = H), m. 225-7°.

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Isoxazole – Wikipedia,
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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Wasylina, L.; Puszko, A. researched the compound: 3,5-Dimethyl-4-nitropyridine 1-oxide( cas:14248-66-9 ).Application In Synthesis of 3,5-Dimethyl-4-nitropyridine 1-oxide.They published the article 《Electronic spectra and structure of methyl derivatives of 4-nitropyridine N-oxide》 about this compound( cas:14248-66-9 ) in Chemistry of Heterocyclic Compounds (New York)(Translation of Khimiya Geterotsiklicheskikh Soedinenii). Keywords: methylnitropyridine oxide dipole moment intramol charge transfer. We’ll tell you more about this compound (cas:14248-66-9).

The UV spectra of seven Me derivatives of 4-nitropyridine N-oxide in ethanol have been examined The electronic spectra were calculated by a modified INDO method. Transition energies, intensities and assignments were compared with UV spectra. Spectroscopic manifestations of intramol. interaction indicate that Me groups modify the electronic interaction between the N-oxide and NO2 groups mainly through a steric strain.

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Name: 3,5-Dimethyl-4-nitropyridine 1-oxide. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Systematic coordination chemistry and cytotoxicity of copper(II) complexes with methyl substituted 4-nitropyridine N-oxides. Author is Puszko, Aniela; Brzuszkiewicz, Anna; Jezierska, Julia; Adach, Anna; Wietrzyk, Joanna; Filip, Beata; Pelczynska, Marzena; Cieslak-Golonka, Maria.

Three new nitrato Cu(II) complexes of di-Me substituted 4-nitropyridine N-oxide were synthesized and characterized by elemental anal., magnetic, spectroscopic, thermal and x-ray methods, resp. They were isolated as trans isomers, mononuclear (μ = 1.70-1.88 μB), five-(1-2) and four-(3) coordinate species [Cu(NO3)2(H2O)L2] where L = 2,3-dimethyl- or 2,5-dimethyl-4-nitropyridine N-oxide and [Cu(NO3)2L2], L = 3,5-dimethyl-4-nitropyridine N-oxide, resp. The x-ray crystal structure of (1) (L = 2,3-dimethyl-4-nitropyridine N-oxide) was determined The organic ligands, the complexes and copper hexaqua ion as a reference were tested in vitro on the cytotoxic activity against human cancer cell lines: MCF-7 (breast), SW-707 (colon) and P-388 (murine leukemia). The complexes are relatively strong cytotoxic agents towards P-388 cell line. Comparative anal. was performed for all known Cu(II) complexes containing Me derivatives of the 4-nitropyridine N-oxide from their composition, structure and cytotoxic activities. To obtain the typical structure for these species (i.e., 4-coordinate mononuclear trans-[Cu(inorganic anion)2L2]), two Me groups must be situated on both sides of N atom(s) (i.e., NO and NO2) in the ligand. The biol. activity is strongly dependent upon the number of the Me groups and the type of cell line. The best cytotoxic results were found for the complexes without substituents or with one Me group. Generally, for all cell lines, the complexation increased cytotoxicity when compared with the free ligands.

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Isoxazole – Wikipedia,
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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide( cas:14248-66-9 ) is researched.Category: isoxazole.Kaneko, Chikara; Yokoe, Ichiro; Yamada, Sachiko published the article 《N-Oxides of 11-deficient N-heteroaromatics. VIII. Photochemical rearrangement of pyridine and quinoline 1-oxides having sterically hindered 4-nitro group》 about this compound( cas:14248-66-9 ) in Tetrahedron Letters. Keywords: PYRIDINES PHOTO REARRANGEMENT; QUINOLINE PHOTO REARRANGEMENT; PHOTO REARRANGEMENT QUINOLINE; REARRANGEMENT PHOTO QUINOLINE. Let’s learn more about this compound (cas:14248-66-9).

EtOH (550 ml.) containing 1 g. 3,5,4-Me2(O2N)C5H2NO irradiated (N atm.) 1.5 hrs. by a Hanovia 450 w. high-pressure Hg-arc lamp placed inside a watercooled pyrex immersion well, the solvent evaporated, and the residue recrystallized from 1:10 MeOH-Me2CO yielded 30% 3,5,4-Me2(HO)C5H2NO, m. 184°, (Hertog and Combe, CA 47, 5938c). A mechanistic pathway involving nitro-nitrite rearrangement as a key step was tentatively suggested. Steric hindrance by the 2 ortho Me groups may prevent abstraction of H from the solvents by the excited species and thus inhibit formation of the 4-hydroxyamino compound Under the above conditions photolysis of 4-nitroquinoline 1-oxide gave only 7% 2,4-dihydroxyquinoline, m. 300°, whereas 3-methyl-4-nitroquinoline 1-oxide gave 30% 3-methyl-2,4-dihydroxyquinoline, m. 264-5°; monoacetate, m. 241-3°. Contrary to the photolysis of 4-nitro derivatives of pyridine, 2-picoline, 3-picoline, and 2,6-lutidine 1-oxides, the presence of O did not affect the formative of these products but the yields of the corresponding 4-hydroxy derivatives were somewhat lower.

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Isoxazole – Wikipedia,
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Computed Properties of C7H8N2O3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about N-Oxides of 11-deficient N-heteroaromatics. VIII. Photochemical rearrangement of pyridine and quinoline 1-oxides having sterically hindered 4-nitro group. Author is Kaneko, Chikara; Yokoe, Ichiro; Yamada, Sachiko.

EtOH (550 ml.) containing 1 g. 3,5,4-Me2(O2N)C5H2NO irradiated (N atm.) 1.5 hrs. by a Hanovia 450 w. high-pressure Hg-arc lamp placed inside a watercooled pyrex immersion well, the solvent evaporated, and the residue recrystallized from 1:10 MeOH-Me2CO yielded 30% 3,5,4-Me2(HO)C5H2NO, m. 184°, (Hertog and Combe, CA 47, 5938c). A mechanistic pathway involving nitro-nitrite rearrangement as a key step was tentatively suggested. Steric hindrance by the 2 ortho Me groups may prevent abstraction of H from the solvents by the excited species and thus inhibit formation of the 4-hydroxyamino compound Under the above conditions photolysis of 4-nitroquinoline 1-oxide gave only 7% 2,4-dihydroxyquinoline, m. 300°, whereas 3-methyl-4-nitroquinoline 1-oxide gave 30% 3-methyl-2,4-dihydroxyquinoline, m. 264-5°; monoacetate, m. 241-3°. Contrary to the photolysis of 4-nitro derivatives of pyridine, 2-picoline, 3-picoline, and 2,6-lutidine 1-oxides, the presence of O did not affect the formative of these products but the yields of the corresponding 4-hydroxy derivatives were somewhat lower.

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Reference of 3,5-Dimethyl-4-nitropyridine 1-oxide. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about Aromaticity and tautomerism. IV. Free energy-enthalpy correlations for protonation of pyridine bases and azine N-oxides and temperature variation of the HO and HA acidity functions. Author is Cook, Michael J.; Dassanyake, Nissanke L.; Johnson, C. David; Katritzky, Alan R.; Toone, Trevor W..

Addnl. data considered in abstracting and indexing are available from a source cited in the original document. Thermodn. parameters for the protonation of 9 weakly basic pyridines and 9 azine N-oxides were obtained from pKa measurements at 25, 40, 60, 80, and 90°. Linear ΔH°-pKa correlations were found. The temperature variations of the H0 and HA acidity functions were examined

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Isoxazole – Wikipedia,
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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide(SMILESS: O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-],cas:14248-66-9) is researched.Electric Literature of C7H13NO2. The article 《Ab initio studies of acid-base reactions in the substituted 4-nitropyridine N-oxide systems》 in relation to this compound, is published in Journal of Molecular Structure: THEOCHEM. Let’s take a look at the latest research on this compound (cas:14248-66-9).

The energies and Gibbs free energies of protonation and homocomplexed cation formation were determined by ab initio methods at the RHF, MP2 levels and in the PCM solvation model for 15 4-nitropyridine derivatives using the 6-311 + G** basis set. The results of ab initio calculations confirmed that the acidity constants in the non-aqueous media studied changed in terms of their substituent effects and the sequence of acidity changes in water. Furthermore, the values of the cationic homoconjugation energy parameters and equilibrium constants increased with increasing basicities of the N-oxides studied. The proton-transfer energy surface in the homoconjugated cation of the 2-methyl-4-nitropyridine N-oxide exhibits a double min., with 2.44 kcal/mol energy barrier. This barrier vanishes when the thermodn. correction is included.

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Isoxazole – Wikipedia,
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Related Products of 14248-66-9. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about The influence of steric effect on 1H NMR, 13C NMR, and IR spectra of methylated derivatives of 4-nitropyridine N-oxide.

The 1H NMR, 13C NMR, and IR spectra of 2-methyl-. 2,3-dimethyl-, 2,5-dimethyl-, 2,6-dimethyl-, 3,5-dimethyl-, and 2,3,6-trimethyl-4-nitropyridine N-oxides were interpreted. The influence of electron properties of substituents on changes of chem. shifts was analyzed. It was found that “”ortho-effect”” of the Me group inhibits paramagnetism of the nitro group. The ratio between a given substituted heterocyclic compound, its parent compound and the identically substituted benzene derivatives has been determined It was found that the effect of the nitro group on chem. shift and the so-called back donation is modified by electronegativity and the position of the substituent.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Derivatives of 4-amino- and 4-nitropyridine, published in 1960, which mentions a compound: 14248-66-9, Name is 3,5-Dimethyl-4-nitropyridine 1-oxide, Molecular C7H8N2O3, Product Details of 14248-66-9.

The following were prepared by conventional procedures. A series of substituted pyridine 1-oxides (substituent given): 3-Et (I), hygroscopic oil, b12 123-5°, picrate, m. 95°; 3-iso-Pr, b0.8 120-2°, picrate, m. 125-6°; 3-tert-Bu (Ia), b1 132-4°, picrate, m. 143-4°; 3,5-Me2, b0.1 116-18°, picrate, m. 135-6°; 2,3,5,6-Me4, needles, m. 139-40°, picrate, m. 144-5°; and 3-Br, -, picrate, m. 144.5-5.5°. I (24.5 g.), 65 ml. concentrated H2SO4 and 34 ml. concentrated HNO3 were warmed to 50° to initiate reaction, then heated 3.5 hrs. at 90-100°, the whole cooled, neutralized with solid K2CO3, filtered, the filtrate extracted with CHCl3 and the CHCl3 concentrated gave 19 g. 3-ethyl-4-nitropyridine 1-oxide (II), yellow needles, m. 68-9°. In similar fashion were prepared the following substd. 4-nitropyridine 1-oxides: 3-iso-Pr, m. 138-9°; 3,5-Me2 (IIa), m. 174-5° (picrate m. 137.5-8.5°); 2,3, 5,6-Me4 (IIb), m. 115-16° (picrate m. 160-1°); 3-Br, m. 156-7° [small amount of 3,4-Br(O2N)C5H3N also formed]. 3-tert-Butyl-2(or 6-)nitropyridine (IIc) m. 104.5-5.5°. To 5 g. II in 100 ml. dry CHCl3 at 0-10° was added 25 ml. PCl3, the whole kept 0.67 hr. at 10° poured on ice, treated with excess NaOH, extracted with CHCl3, and the CHCl3 extracts concentrated to give 3.8 g. 3,4-Et(O2N)C5H3N, b0.25 56-8°. Similarly were prepared 3,4-iso-Pr(O2N)C5H3N, b0.85 82-4° (picrate m. 106-7°); 3,5,4-Me2(O2N)C5H2N.0.5.H2O, m. 38-9° (picrate m. 169-70°); and 2,3,5,6,4-Me4(O2N)C5N.2H2O, m. 198-200° (picrate m. 174-6°). To 13 g. II was added 60 ml. AcCl; a vigorous reaction occurred. Subsequently, the mixture was poured on ice, the whole treated with excess NaOH and the product isolated via CHCl3 extraction to give 8.2 g. 4-chloro-3-ethylpyridine 1-oxide (IId), m. 86° (picrate m. 137-8°). The following substituted 4-chloropyridine 1-oxides were similarly prepared: 3-iso-Pr, hygroscopic, m. 87-8° (picrate m. 130-1°); 3,5-Me2 (III), m. 201-2° (picrate m. 142-3°); 2,3,5,6-Me4, m. 153-4° (picrate m. 154-5°); 3-Br, m. 153.5-4.5° (picrate m. 120-1°). III (2.5 g.) and 18 ml. concentrated aqueous NH3 heated 18 hrs. at 140°, the whole cooled, treated with 2.5 g. K2CO3, evaporated to dryness and the residue extracted with AcEt gave 1.6 g. 4-amino-3,5-dimethylpyridine 1-oxide-2H2O (IV), m. 227-9°, picrate m. 221-3°. 3,4-Me(O2N)C5H3N (2.5 g.), 50 ml. EtOH, 4 ml. 90% H2NNH2.H2O, and a small amount of Raney Ni (V) were heated 0.5 hr. on the steam bath, more V added, the whole filtered, and the filtrate concentrated to give 1.2 g. 3,4-Me(H2N)C5H3N, m. 108-9°. This procedure also gave 3,4-Et(H2N)C5H3N.0.5.H2O, m. 52-3° (picrate m. 196-7°); 3,4-iso-Pr(H2N)C5H3N.0.5.H2O, m. 69-70° (picrate m. 156-7°). To 0.5 g. IV in 5 ml. AcOH was added 0.3 g. Fe dust, the whole heated 1.5 hrs. on the steam bath, cooled, treated with excess NaOH and the product isolated via Et2O extraction to give 0.2 g. 3,5,4-Me2(H2N)C5H2N.2H2O (VI), m. 83-4° (picrate m. 226-7°). Alternately, 2 g. IIa, 25 ml. MeOH, 2 g. Raney Ni, and H gave 1.1 g. VI; the same procedure with IIb gave the amino derivative hemihydrate m. 196-7° (picrate m. 225-6°). Both reduction procedures with IIc gave the amino derivatives, m. 128-9°, λ 292, 228 mμ (log ε 3.56, 4.9) (picrate m. 242°). IId (3 g.) and 18 ml. 30% aqueous MeNH2 heated 18 hrs. at 140° gave, as above with IV, 2.1 g. 3-methyl-4-methylaminopyridine 1-oxide (VII), m. 106-7° (picrate m. 184-5°). Similarly were prepared the following substituted 4-methylaminopyridine 1-oxides: 3-Et, b0.5 120-2°, m. 117-18° (picrate m. 182-3°); 3-iso-Pr (VIII) (no m.p. given) (picrate m. 164-5°); 3,5-Me2, m. 94.5-5.5° (picrate m. 172-3°); 3-Br, hygroscopic solid (picrate m. 189-91°) and 2,3,5,6-Me4, hygroscopic solid (picrate m. 140-1°). VII reduced by Fe in AcOH gave 3,4-Me(MeNH)C5H3N, m. 125-6° (picrate m. 199-200°). VIII hydrogenated as above gave 3,3-iso-Pr-(MeNH)C5H3N, m. 95-6° (picrate m. 159-60°) and this procedure gave the following 3-substituted 4-(MeNH)C5H3N derivatives): 3,5-Me2, m. 119.5-20.5° (picrate m. 194.5-5.5°); 2,3,5,6-Me4, m. 118-19° (picrate m. 160-1°); 3-Br, 92-3°. The following were prepared by the above procedures: 3,4-Me(Me2N)C5H3N (IX), b1 73-5° (picrate m. 172-3°) and IX 1-oxide, b0.15 142-4° (picrate m. 130-1°); 3,4-Et(Me2N)C5H3N (X), b0.6 82-3° (picrate m. 118-19°) and X 1-oxide, b1 178-80° (picrate m. 139-40°); 3,4-iso-Pr-(Me2N)C5H3N (XI), b0.45 79-80° (picrate m. 138-9°) and XI 1-oxide, – (picrate m. 151-2°); 3,5,4-Me2(Me2N)C5H2N (XII), b0.4 69-7° (picrate m. 172-3°) and XII 1-oxide m. 83-4° (picrate m. 115-16°); and 3,4-Br(Me2N)C5H3N (XIII), b0.5 82-4° (picrate m. 182-3°) and XIII 1-oxide, – (picrate m. 160-1°). Ia (3.5 g.) and SO2Cl2 heated 2 hrs. at 110-20° gave 2 products, C9H12ClN, giving picrates, m. 152-3° and 149-50°.

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Isoxazole – Wikipedia,
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