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

HRID 17537Notes

Reaction equation

HRID 17537 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
72.5 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cd8d1709fc024f3a9cf523ecc46a0a6f
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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