Stannous Chloride → 1-Chloro-6-methylisoquinolin-5-amine

Participants

Reaction Conditions

Reaction Steps

Tin (II) chloride (0.43 g, 2.2 mmol) was added to a solution of 1-chloro-6-methyl-5-nitroisoquinoline (0.100 g, 0.45 mmol) in ethanol/DCM (10.0 mL, 4:1). The solution was heated at 70° C. for 16 h. The reaction mixture was diluted with DCM and the organic phase was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown solid which was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford 1-chloro-6-methylisoquinolin-5-amine (0.035 g, 40% yield) as a brown solid. MS (ESI, pos. ion) m/z: 193 [M+H]+

Provenance & Evidence