2-Bromo-5-nitrobenzoic acid → 5-Amino-2-bromobenzoic acid

HRID 584861Notes

Reaction equation

HRID 584861 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H][H]>CO.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 2430252-Bromo-5-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 27696245-Amino-2-bromobenzoic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-bromo-5-nitrobenzoic acid (1.10 g, 4.06 mmol) (Aldrich, 38, 184-5), activated Pd—C (43.62 mg, 0.41 mmol) (Aldrich, 20, 569-9) in methanol (30 ml) was hydrogenated for 4 hr under 30 psi of hydrogen pressure. After the mixture was filtered, the filtrate was concentrated to give 0.80 g (91.2% yield) of 5-amino-2-bromobenzoic acid as a pale yellow solid.

Workup

  1. filtrationAfter the mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6f9c76d053394dd9bed2be85889dee2e
Source dataset
uspto-grants-2005_08
Patent number
US06927303B2

Reaction notes

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