Dimethylformamide → 3-Phenoxy-6,7-dimethylquinoline

Participants

Reaction Steps

To a solution of Nail (1.2g; 60% disp in oil) in DMF (3 ml) is added 3-hydroxy-6.7-dimethoxyquinoline (150 mg; 0.73 tool) and the reaction mixture is allowed to stir for 30 minutes at room temperature. To this is added the tetrafluoroborate salt of chlorobenzene manganese tricarbonyl complex (prepared by J.O.C. 24: 1991;7092) (183 mg) and stirred for 3 hours. To this is added 20 ml of acetonitrile and stirred overnight. The reaction mixture is dissolved in EtOAc: brine and extracted 2× with EtOAc, washed with water 2×, washed with brine, dried (MgSO4) and concentrated in vacuo to obtain a material which is purified by FPLC using 1% methanol: chloroform to obtain a solid which NMR indicates to be 3-phenoxy-6.7-dimethoxyquinoline. The hydrochloride salt is then prepared in the usual manner m.p. 224-226).

Provenance & Evidence