Anthranilic Acid → 2-(Nitroamino)benzoic acid

反応式

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]

参加物

反応物 4

HCID 227Anthranilic Acid

HCID 944Nitric Acid

HCID 1118Sulfuric Acid2 回

HCID 14923Ammonium Hydroxide

生成物 1

HCID 215441192-(Nitroamino)benzoic acid収率 75.4%

実験手順

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).