Diazomethane → Methyl 2-amino-3-nitrobenzoate

HRID 1470654Notes

Reaction equation

HRID 1470654 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:16])=[N-]>CO>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 607264Methyl 2-amino-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-3-nitro-benzoic acid (6 g, 33 mmol) in methanol (20 mL), an ethereal solution of diazomethane gas was added until the staring material is completely consumed. The reaction mixture was then evaporated under reduced pressure and the crude resulting solid was purified by flash column chromatography using 5% ethylacetate & hexane as an eluent, to obtain 2 g of the required product as a yellow coloured solid.

Workup

  1. customis completely consumed
  2. customThe reaction mixture was then evaporated under reduced pressure
  3. customthe crude resulting solid
  4. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-f522bbd5f1814969be4525f9d331c233
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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