Dimethyl 2-(3-nitropyridin-2-yl)malonate → 2-Methyl-3-nitropyridine

HRID 2201401ノート

反応式

HRID 2201401 の反応式
COC(=O)[CH:4]([C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1)C(OC)=O>Cl>[CH3:4][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1

参加物

3

反応物 1

HCID 2782199Dimethyl 2-(3-nitropyridin-2-yl)malonate

生成物 1

HCID 3293602-Methyl-3-nitropyridine収率 92.7%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A modified procedure of Cash et al. (Org. Biomol. Chem. 2005, 3. 3701-3706) was used. Dimethyl-2-(3-nitropyridin-2-yl)malonate (1.4 g, 5.5 mmol) was dissolved in 70 ml 6 M HCl and refluxed for 8 h. After neutralization with saturated Na2CO3 solution the solution was extracted three times with dichloromethane. The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by bulb tube distillation (0.35 mbar; 70-80° C.). 2-Methyl-3-nitropyridine (0.7 g, 5.1 mmol, 92%) was obtained as a pale yellow oil. 1H NMR (300 MHz, CDCl3) 8.72 (pdd; 3J=1.2 Hz; 3J=4.7 Hz; 1H; H-6); 8.27 (pdd; 3J=1.2 Hz; 3J=8.2 Hz; 1H; H-4); 7.35 (pdd; 3J=4.7 Hz; 3J=8.2 Hz; 1H; H-5); 2.86 (s; 3H; CH3).

後処理

  1. temperaturerefluxed for 8 h
  2. extractionAfter neutralization with saturated Na2CO3 solution the solution was extracted three times with dichloromethane
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by bulb tube
  7. distillationdistillation (0.35 mbar; 70-80° C.)

出典と根拠

ORDレコード
ord-e12327c3bb024bcd89e22da162dd200e
出典データセット
uspto-grants-2016_06
特許番号
US09364459B2

反応ノート

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