Chloride → Methyl 4-amino-3-nitrobenzoate

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Cl-].[CH3:15]O>>[CH3:15][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

Reactant 3

HCID 312Chloride

HCID 887Methanol

HCID 74115Benzoic acid, 4-amino-3-nitro-

Product 1

HCID 3941008Methyl 4-amino-3-nitrobenzoateYield 81%

Procedure

To a mixture of 4-amino-3-nitro-benzoic acid (10.0 g, 54.9 mmol) suspended in methanol (150 mL) was added thiony chloride (3.99 mL, 54.9 mmol). The mixture was heated to reflux overnight, then cooled to room temperature and filtered. The solid recovered by filtration was rinsed with cold methanol and dried to give 8.68 g (81%) of 4-amino-3-nitro-benzoic acid methyl ester.