Water → Methyl 4-bromo-2-(isopropylamino)benzoate

HRID 2220369Notes

Reaction equation

HRID 2220369 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:15])=[O:7])=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 248246474-Bromo-2-(isopropylamino)benzoic acid

Product 1

HCID 24824349Methyl 4-bromo-2-(isopropylamino)benzoateYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-bromo-2-(isopropylamino)benzoic acid (448 mg) and potassium carbonate (480 mg) in N,N-dimethylformamide (9 ml) was added methyl iodide (162 μl) at room temperature and the mixture was stirred at the same temperature for 1 hour. To the mixture was added water (20 ml) and extracted with mixed solvent (hexane/ethyl acetate=1/1). The organic layer was washed with brine, dried over magnesium sulfate and evaporated to give methyl 4-bromo-2-(isopropylamino)benzoate (443 mg).

Workup

  1. extractionextracted with mixed solvent (hexane/ethyl acetate=1/1)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d9973bfd20f140c694cb5dda5f0510f8
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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