Diethyl Oxalate → Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

HRID 1693352

반응식

HRID 1693352 반응식
[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]>C(OCC)C.C(O)C>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])[CH3:14]

참가 물질

6

반응물 3

HCID 7268Diethyl OxalateHCID 5218284-Methyl-3-nitropyridineHCID 23670592Potassium ethoxide

생성물 1

HCID 23269548Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of potassium ethoxide (3.1 g, 36.2 mmol) in diethyl ether (70 mL) and ethanol (10 mL) under an argon atmosphere was added diethyl oxalate (4.9 mL, 36.2 mmol) and the reaction stirred at rt for 30 min. A solution of 4-methyl-3-nitropyridine (5.0 g, 36.2 mmol) in diethyl ether (20 mL) was added resulting in the immediate formation of a dark red precipitate. The reaction mixture was stirred at rt for 72 h, then cooled to 0° C. and filtered. The solid was dissolved in water (500 mL) acidified to pH 4 with acetic acid and the precipitate collected and dried to give the title compound as a red solid. δH (d6 DMSO): 1.27 (3H, t), 4.25 (2H, q), 6.74 (1H, s), 8.34 (1H, d), 8.43 (1H, d), 8.98 (1H, s); m/z (ES+)=239 [M+H]+.

후처리

  1. customresulting in the immediate formation of a dark red precipitate
  2. stirringThe reaction mixture was stirred at rt for 72 h
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in water (500 mL)
  6. customthe precipitate collected
  7. customdried

출처 및 근거

ORD 기록
ord-478fe2ca9e2e42b381fc2503cdd81988
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158622B2

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