5-Fluoro-2-methyl-8-nitro-1,2-dihydroquinoline → 5-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-amine

Participants

Reaction Steps

A suspension of 10% Pd/C (30 mg) in a mixture of IMS (3 mL) and EtOAc (5 mL) was stirred under an atmosphere of hydrogen for 15 min before a solution of 5-fluoro-2-methyl-8-nitro-1,2-dihydroquinoline (76.8 mg, 0.369 mmol) in EtOAc (15 mL) was added. The reaction mixture was stirred at RT under a hydrogen atmosphere for 20 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo affording a mixture of the title compound and 5-fluoro-2-methylquinolin-8-ylamine as a purple oil. LCMS (Method J): RT 1.90 min (28%) [M+H]+ 181 and 2.26 min (42%) [M+H]+ 177

Provenance & Evidence