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

HRID 17537노트

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HRID 17537 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 68586212Methyl 4-acetamido-5-bromo-2-hydroxybenzoate수율 45%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
72.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cd8d1709fc024f3a9cf523ecc46a0a6f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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