Hydrochloric Acid → 3-Bromo-4-carbamoylbenzoic acid

HRID 906166Notes

Reaction equation

HRID 906166 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([NH2:14])=[O:13])[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([NH2:14])=[O:13])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67403808Methyl 3-bromo-4-carbamoylbenzoate

Product 1

HCID 577484673-Bromo-4-carbamoylbenzoic acidYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-bromo-4-(aminocarbonyl)benzoate (0.54 mmol) was dissolved in methanol (1 mL) and was treated with 1M aqueous sodium hydroxide (1 mL) at 45° C. for 3 h. The reaction mixture was cooled to room temperature and concentrated to afford an aqueous residue that was acidified with 1N aqueous hydrochloric acid to pH ˜3. The precipitate was collected by filtration, washed with water, and dried to afford 3-bromo-4-(aminocarbonyl)benzoic acid (69.4 mg, 0.28 mmol, 53% overall). 1H NMR (400 MHz, d6-DMSO): 13.47 (br s, 1H), 8.08 (dd, 1H), 8.00 (br s, 1H), 7.94 (dd, 1H), 7.73 (br s, 1H), 7.51 (d, 1H); MS (EI) for C8H6BrNO3: 242, 244(M−H).

Workup

  1. concentrationconcentrated
  2. customto afford an aqueous residue that
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-01da857cd7dd44ff80a58d05f77db90e
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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