Dimethylformamide → 5-Bromo-1-(sec-butyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1526377ノート

反応式

HRID 1526377 の反応式
[CH:1]([N:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([C:13]#[N:14])[C:6]1=[O:15])([CH2:3][CH3:4])[CH3:2].[Br:16]N1C(=O)CCC1=O.CN(C)C=O>C(=O)([O-])O.[Na+]>[Br:16][C:9]1[C:8]([O:11][CH3:12])=[C:7]([C:13]#[N:14])[C:6](=[O:15])[N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH:10]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 1177700381-(Sec-butyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile

生成物 1

HCID 1177706575-Bromo-1-(sec-butyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile収率 72.3%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 1-(sec-butyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step A (260 mg), N-bromosuccinimide (269 mg) and N,N-dimethylformamide (3 mL) was stirred at 60° C. for 2 hr 30 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted threetimes with ethyl acetate. The extracts were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (260 mg).

後処理

  1. extractionthe mixture was extracted threetimes with ethyl acetate
  2. washwashed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-b4baa0a0118742dcb9303ba12dfa093c
出典データセット
uspto-grants-2015_07
特許番号
US09085578B2

反応ノート

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