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

HRID 1470622Notes

Reaction equation

HRID 1470622 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Cl: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]([Cl:14])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 2320552-Amino-5-chloro-3-nitrobenzoic acid

Product 1

HCID 615489Methyl 2-amino-5-chloro-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-5-chloro-3-nitro-benzoic acid (2 g, 1.0 mmol) in methanol (100 mL) was added a saturated ethereal solution of diazomethane gas (50 mL) till all 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 (1.8 g, 84.11%).

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-d06d9bf51a264e35af1a34157235202a
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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