Hydrochloric Acid → Methyl 2-amino-5-bromo-3-nitrobenzoate

HRID 1010657Notes

Reaction equation

HRID 1010657 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[NH:14]C(=O)C(F)(F)F.Cl>CO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[NH2:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59337630HCID 59337630, compound

Product 1

HCID 17984898Methyl 2-amino-5-bromo-3-nitrobenzoateYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of 5-Bromo-3-nitro-2-(2,2,2-trifluoro-acetylamino)-benzoic acid methyl ester (8 g, 21.56 mmol) in methanol (150 ml) was treated with hydrochloric acid (6M, 75 ml) and heated at 80° C. for 16 h. After cooling to ambient temperature, the yellow solid was collected by filtration and washed with cold water and dried in vacuo to give 2-Amino-5-bromo-3-nitro-benzoic acid methyl ester (5.0 g, 84%).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe yellow solid was collected by filtration
  3. washwashed with cold water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-073d4daeaf5b460988431cd648ee805a
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

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