Dimethylformamide → Methyl 4-acetamido-5-bromo-2-hydroxybenzoate

HRID 17537ノート

反応式

HRID 17537 の反応式
[Br:1]N1C(=O)CCC1=O.CN(C)C=O.[C:14]([NH:17][C:18]1[CH:19]=[C:20]([OH:28])[C:21](=[CH:26][CH:27]=1)[C:22]([O:24][CH3:25])=[O:23])(=[O:16])[CH3:15]>C(OCC)(=O)C>[C:14]([NH:17][C:18]1[CH:19]=[C:20]([OH:28])[C:21](=[CH:26][C:27]=1[Br:1])[C:22]([O:24][CH3:25])=[O:23])(=[O:16])[CH3:15]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 77719Methyl 4-acetamidosalicylate

生成物 1

HCID 68586212Methyl 4-acetamido-5-bromo-2-hydroxybenzoate収率 45%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
72.5 °C

実験手順

N-Bromosuccinimide (0.94 g, 5.3 mmol) was added to an N,N-dimethylformamide (8 ml) solution of methyl 4-acetylaminosalicylate (I-248) (1.1 g, 5.0 mmol), followed by stirring with heating under reflux at 70 to 75° C. for 2 hours and a half. After cooling to room temperature, ethyl acetate was added, followed by washing twice with saturated brine and drying over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform/methanol (100:1) gave the entitled compound (0.64 g, 45%) as a pale red solid.

後処理

  1. temperaturewith heating
  2. temperatureAfter cooling to room temperature
  3. washby washing twice with saturated brine
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure

出典と根拠

ORDレコード
ord-cd8d1709fc024f3a9cf523ecc46a0a6f
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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