Methyl 2-(3-chloro-5-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate → Methyl 2-(3-amino-5-chlorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Participants

Reaction Steps

To a solution of methyl 2-(3-chloro-5-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (124 mg, 0.33 mmol) in ethanol/water (2 mL/0.5 mL) was added 2 drops of conc. hydrochloric acid and iron (370 mg, 6.62 mmol). The mixture was stirred and heated to reflux for 4 h. LC-MS showed most of SM was consumed. The mixture was dried over silica gel and washed through a short column with petroleum ether:ethyl acetate=3:1 to afford 95 mg of methyl 2-(3-amino-5-chlorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a brown solid. (Yield=83%). MS (ESI+APCI) M+1=345.

Provenance & Evidence