Anthranilic Acid → 2-(Nitroamino)benzoic acid

Reaction equation

S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[N+:16]([O-])([OH:18])=[O:17].[NH4+].[OH-]>>[N+:16]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])([O-:18])=[O:17]

Participants

Reactant 4

HCID 227Anthranilic Acid

HCID 944Nitric Acid

HCID 1118Sulfuric Acid2×

HCID 14923Ammonium Hydroxide

Product 1

HCID 215441192-(Nitroamino)benzoic acidYield 75.4%

Procedure

To a solution of concentrated sulfuric acid (2 mL) was slowly added 2-aminobenzoic acid (CXXIV) (1.0 g, 7.24 mmol). A mixture of concentrated sulfuric acid (1.5 mL) and fuming nitric acid (1.5 mL) was then slowly added and the reaction was stirred at room temperature overnight. The reaction mixture was poured into crushed ice and treated with aqueous NH4OH until pH 3.0. The yellow-orange solid was washed with cold water and dried to produce 2-(nitroamino)benzoic acid (CXXV) as a yellow solid (1.0 g, 5.46 mmol, 75.4% yield). The crude product was used for the next step without further purification. ESIMS found for C7H6N2O4 m/z 183.9 (M+H).