Hydrazine → HCID 67165184, compound

Participants

Reaction Conditions

Reaction Steps

Crude 2-benzoyl-6-chloro-1,2,3,9-tetrahydro-β-carbolin-4-one (4 g) was dissolved in 30 ml of anhydrous hydrazine and stirred at reflux (130° C. oil bath) under N2 for 6 hours, after which the reaction mixture was allowed to cool to room temperature and sit overnight. The precipitated yellow solids were removed by filtration and washed with water, 2×5 ml, to yield 785 mg (30%) of 4-amino-6-chloro β-carboline as an off white solid. Additional water was added to the combined filtrates until no further precipitation occurred. These solids were also removed by filtration to give 1.056 g (39%) of 4-amino-6-chloro β-carboline as yellow solids, (69% total yield). 1H-NMR (300 MHz, DMSO-d6): δ 11.48 (s, 1H), 8.44 (s, 1H), 8.13 (s, 1H), 7.77 (s, 1H), 7.42-7.52 (m, 2H), 5.86 (s, 2H). Formic acid standard conditions. DAD RT=1.68 min. M+H=218.

Provenance & Evidence