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

HRID 751619

反応式

HRID 751619 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-012a2cae1fe2468fa90312d42541e3d5
出典データセット
uspto-grants-2008_07
特許番号
US07405210B2

関連ノート

読み込み中…