Acetic Acid → Ethyl 2-bromo-5-nitro-α-oxo-4-pyridinepropanoate

HRID 751619

반응식

HRID 751619 반응식
[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[Br:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1.C(O)(=O)C>C(OCC)C.C(O)C.O>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:22][C:20]1[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=[C:16]([Br:15])[CH:21]=1)[CH3:14]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 3458732-Bromo-4-methyl-5-nitropyridineHCID 23670592Potassium ethoxide

생성물 1

HCID 59753623Ethyl 2-bromo-5-nitro-α-oxo-4-pyridinepropanoate

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of potassium ethoxide (2.05 g, 24.3 mmol) in diethyl ether (70 mL) and ethanol (10 mL) under an argon atmosphere was added diethyl oxalate (3.3 mL, 24.3 mmol) and the reaction stirred at rt for 15 min. A solution of 2-bromo-4-methyl-5-nitropyridine (Preparation 24, 4.8 g, 22.1 mmol) in diethyl ether (20 mL) was added to the reaction mixture giving an immediate black precipitate. The reaction was allowed to stir at rt for 6 h, then cooled to 0° C. and filtered to give a black solid. The solid was dissolved in water (250 mL) and acidified to pH 4 with acetic acid resulting in formation of a red precipitate. The solid was collected and dried to give the title compound as a red solid. δH (d6 DMSO): 1.16 (3H, t), 4.01 (2H, q), 6.55 (1H, s), 7.92 (1H, s), 8.96 (1H, s).

후처리

  1. customgiving an immediate black precipitate
  2. stirringto stir at rt for 6 h
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. customto give a black solid
  6. customThe solid was collected
  7. customdried

출처 및 근거

ORD 기록
ord-012a2cae1fe2468fa90312d42541e3d5
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405210B2

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