Diazomethane → Methyl 2-amino-5-bromo-3-nitrobenzoate

HRID 1470599Notes

Reaction equation

HRID 1470599 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Br:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:17])=[N-]>CO>[CH3:17][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Br:14])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 184314782-Amino-5-bromo-3-nitrobenzoic acid

Product 1

HCID 17984898Methyl 2-amino-5-bromo-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-5-bromo-3-nitro-benzoic acid (5 g, 19.15 mmol) in methanol (100 mL) was added a saturated ethereal solution of diazomethane gas (75 mL) until the starting material was consumed. The reaction mixture was concentrated to dryness and the residue obtained was purified by column chromatography using 5% ethyl acetate in hexane as an eluent to obtain the title compound as yellow solid which was directly used for the next step (5 g, 94.3%).

Workup

  1. customwas consumed
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customthe residue obtained
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-46d0d4921868417d9b7c845fef352050
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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