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

HRID 2201401노트

반응식

HRID 2201401 반응식
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

참가 물질

3

반응물 1

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

생성물 1

HCID 3293602-Methyl-3-nitropyridine수율 92.7%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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).

후처리

  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.)

출처 및 근거

ORD 기록
ord-e12327c3bb024bcd89e22da162dd200e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09364459B2

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