Water → HCID 11126561, compound

Participants

Reaction Steps

(±) 1-Methyl-7-nitro-3,4-dihydroisoquinoline (2.0 g, 10.5 mmol) was dissolved in ethanol (150 ml) and heated to 60° C., before treatment with a solution of tin (II) chloride dihydrate (9.5 g, 42.1 mmol) in conc. HCl (30 ml). The resultant mixture was heated at 60° C. for 1 h. After cooling, the reaction mixture was poured into water (200 ml) and basified (pH 9) with KOH pellets, liberating an oily residue. This residue was extracted into dichloromethane and dried over magnesium sulfate. Purification by chromatography through silica gel, eluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2) yielded the title compound as a dark brown oil (0.93 g, 55%).

Provenance & Evidence