Hydrazine → 9-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carbohydrazide

Participants

Reaction Steps

A mixture of methyl 9-(2,5-dichlorobenzyl)-9H-β-carboline-3-carboxylate (4.8 g, 12.5 mmole), hydrazine (6 mL) and methanol (50 mL) was refluxed for 5 hours. The reaction mixture was cooled to room temperature, and the precipitate was collected by filtration. The solid was treated with methanol (50 mL) and the slurry stirred for 10 minutes, filtered, and dried, affording 4.6 grams (98%) of the title compound. 1H NMR (DMSO-d6) δ9.5 (s, 1H), 8.8 (s, 1H), 8.7 (s, 1H), 8.25 (d, 1H), 7.6-7.4 (m, 3H), 7.2-7.1 (m, 2H), 6.5 (s, 1H), 5.7 (s, 2H), 4.3 (s, 2H) MS (APCI; (M+H)+) m/z 385.

Provenance & Evidence