Potassium Carbonate → 2-amino-5-phenylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

1 g (4.62 mmol) of 5-bromoanthranilic acid (Fluka Buchs, Switzerland) and 6.94 ml 1M K2CO3 are stirred in 10 ml DMF. Argon gas is bubbled through the solution. 50 mg tetrakis-triphenylphosphin-palladium (Fluka) and 846 mg (6.94 mmol) phenylboronic acid (Fluka, Buchs, Switzerland) are added. The reaction mixture is stirred for 15 h at 80° C. (tlc-control). The solvent is evaporated, and 50 ml 4N NaOH are added to the residue. The aqueous phase is washed three times with ethyl acetate. Hydrochloric acid is added to the water phase until pH=7 is reached and the aqueous phase is extracted four times with ethyl acetate. After drying the organic phase with MgSO4, the solvent is evaporated and the residue crystallized from CH2Cl2-methanol-hexane. mp: 245° C. (dec.); MS: 214 (M++1); HPLC: tret=9.74 min (Grad 1).

Provenance & Evidence