[ CAS No. 32896-91-6 ] {[proInfo.proName]}

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Quality Control of [ 32896-91-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 32896-91-6 ]

Product Details of [ 32896-91-6 ]

CAS No. :	32896-91-6	MDL No. :	MFCD01646143
Formula :	C₆H₆N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	154.12	Pubchem ID :	-
Synonyms :

Safety of [ 32896-91-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 32896-91-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 32896-91-6 ]
Downstream synthetic route of [ 32896-91-6 ]

[ 32896-91-6 ] Synthesis Path-Upstream 1~1

1
[ 32896-91-6 ]
[ 14150-94-8 ]

Reference： [1] Journal of the Chemical Society, 1951, p. 2590,2593

[ 32896-91-6 ] Synthesis Path-Downstream 1~53

1
[ 6332-56-5 ]
[ 77-78-1 ]
[ 32896-91-6 ]

Reference： [1]Journal of the Chemical Society,1954,p. 4516,4520

2
[ 32896-91-6 ]
3-imino-1-methyl-3,4-dihydro-1<i>H</i>-pyridin-2-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1954,p. 4516,4520

3
[ 32896-91-6 ]
[ 14150-94-8 ]

Reference： [1]Journal of the Chemical Society,1951,p. 2590,2593

4
[ 32896-91-6 ]
[ 33631-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium 10% on activated carbon; hydrogen; for 16h;Sonication; Inert atmosphere;	General procedure: 1-Methyl-3-nitropyridin-2(1H)-one 6 (0.620 g), 1-Benzyl-3-nitropyridin-2(1H)-one 9 (2.0 g) or Ethyl 2-(4'-methyl-3'-nitro-2'-oxopyridin-1'(2H)-yl)acetate 20 (2.00 g) and 10% Pd/C (11% w/w)was flushed with nitrogen then degassed (sonication) ethanol (60or 200 mL) was added under nitrogen. The resulting suspensionwas then flushed with H2 and hydrogenated for 16 h under balloonpressure. The reactionwas quenched by flushing with nitrogen andaddition of Celite. The resulting suspension was filtered through apad of Celite and activated charcoal, using ethyl acetate to washthe plug. The solvent was removed under reduced pressure to givecrude compound as an unstable oil, which was used directly in thenext step. 8.2.2.1. 3-Amino-1-methylpyridin-2(1H)-one 7. Unstable pale yellow/green oil, (0.498 g, 100%). Rf 0.45 (isopropyl alcohol:dichloromethane1:9 with 0.5% triethylamine).
	With palladium on activated charcoal; hydrogen; In methanol; at 40℃; for 5h;	NaH (1.1 equiv) was slowly added at 0C to a 3-nitropyridin-2(1H)-one (1 equiv) solution in THF. The reaction mixture was stirred at 0C for 0.5h. Iodomethane (1 equiv) was then added and the mixture was stirred at 55C for 6h. The reaction was diluted with H2O and extracted thrice with EA, and the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford crude product 16. Intermediate 16 (1 equiv) was dissolved in methanol, and Pd/C (0.1 equiv) was added. The flask was flushed with H2 and stirred for 5hat 40C. The reaction mixture was filtered, concentrated and purified by chromatography to afford intermediate 17.

Reference： [1]Heterocycles,1990,vol. 31,p. 2201 - 2204
[2]European Journal of Medicinal Chemistry,2017,vol. 127,p. 341 - 356
[3]Organic Letters,2018,vol. 20,p. 4062 - 4066
[4]European Journal of Medicinal Chemistry,2019,vol. 183

6
1-methyl-3-nitro-pyridone-⁽²⁾-nitrimide [ No CAS ]
[ 32896-91-6 ]

Reference： [1]Chemische Berichte,1925,vol. 58,p. 1717

7
[ 74-88-4 ]
silver-salt of 3-nitro-pyridin-2-ol [ No CAS ]
[ 20265-35-4 ]
[ 32896-91-6 ]

Reference： [1]Canadian Journal of Chemistry,1953,vol. 31,p. 1181,1183,1186

8
[ 32896-91-6 ]
[ 513-81-5 ]
[ 70411-86-8 ]
cis-4a,5,8,8a-tetrahydro-2,6,7-trimethyl-8a-nitro-1(2H)-isoquinolone [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 601 - 605

9
[ 6332-56-5 ]
[ 74-88-4 ]
[ 32896-91-6 ]

Yield	Reaction Conditions	Operation in experiment
98%		General procedure: Sodium hydride (95%, 1.5 or 2.0 equivalents) was added in portionsto 2-hydroxy-3-nitro pyridine 5 (0.200 g or 2.00 g) or 4-methyl-3-nitropyridin-2(1H)-one 19 (0.663 g) in dry THF (20 or50 mL). The resulting suspension was stirred for 30 min. Methyliodide (1.1 equivalents), benzyl bromide (2.0 equivalents) or ethylbromoacetate (1.1 equivalents) was added dropwise. The resultingyellow suspensionwas heated to 55C under nitrogen for 16 h (6, 9)or 36 h (20). The red reaction mixture was filtered and the solidthoroughly washed with ethyl acetate. The filtrate was concentratedunder reduced pressure. The crude product was purified bysilica column chromatography (as indicated below; 6, 9, and 20). 8.2.1.1. 1-Methyl-3-nitropyridin-2(1H)-one 6. Chromatography(0-20% ethyl acetate/dichloromethane gradient, with 0.5% Et3N).Yellow solid (0.216 g, 98%): M.p 172-176 C (dec.) (Lit. [57] 176 C).FTIR (KBr) nu: 3432, 3085, 1683, 1593, 1540, 1340, 1279, 1111, 915,768 cm-1. 1H NMR (400 MHz, CDCl3) delta: 3.65 (s, 3H, CH3), 6.27 (dd,1H, J = 7.6, 6.8 Hz, H5), 7.70 (dd, 1H, J= 6.4, 2.0 Hz, H6), 8.28 (dd, 1H,J =7.6, 2.0 Hz, H4). 13C NMR (100 MHz, CDCl3) delta: 38.8 (CH3), 103.2(C5), 138.6 (C3, C4), 144.7 (C6), 154.8 (C2). ESI-MS m/z 176.8(M+Na+), 160.8 (M+Li+).
		NaH (1.1 equiv) was slowly added at 0C to a 3-nitropyridin-2(1H)-one (1 equiv) solution in THF. The reaction mixture was stirred at 0C for 0.5h. Iodomethane (1 equiv) was then added and the mixture was stirred at 55C for 6h. The reaction was diluted with H2O and extracted thrice with EA, and the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford crude product 16. Intermediate 16 (1 equiv) was dissolved in methanol, and Pd/C (0.1 equiv) was added. The flask was flushed with H2 and stirred for 5hat 40C. The reaction mixture was filtered, concentrated and purified by chromatography to afford intermediate 17.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 341 - 356
[2]Russian Chemical Bulletin,2001,vol. 50,p. 460 - 463
[3]Organic Letters,2018,vol. 20,p. 4062 - 4066
[4]Organic Letters,2018,vol. 20,p. 5167 - 5171
[5]European Journal of Medicinal Chemistry,2019,vol. 183

10
[ 32896-91-6 ]
3-[(3',4'-dichlorobenzyl)amino]-1-methylpyridin-2(1H)-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 341 - 356

11
[ 32896-91-6 ]
4-(4-fluorophenyl)-3,3-dimethyl-N-(1-methyl-2-oxo-1,2-dihydropyridin-3-yl)butyramide [ No CAS ]