Diethyl Ether → Methyl 2-amino-5-methyl-3-nitrobenzoate

HRID 1470605Notes

Reaction equation

HRID 1470605 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:15]COCC>CO>[CH3:15][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([CH3:14])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 2319842-amino-5-methyl-3-nitrobenzoic acid

Product 1

HCID 58213211Methyl 2-amino-5-methyl-3-nitrobenzoateYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-5-methyl-3-nitro-benzoic acid (5 g, 24 mmol) in a mixture of methanol & ether (8:2, 50 mL), a freshly generated diazomethane gas collected in ether was added until the reaction completes. The reaction mixture was evaporated under reduced pressure and was purified by flash column chromatography using 5% ethyl acetate in hexane as an eluent to get 4.5 g (83%) of the required product as a yellow coloured solid.

Workup

  1. customa freshly generated diazomethane gas collected in ether
  2. additionwas added until the reaction
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-f8323d5b015346938e35b00d91281bf2
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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