Sodium Bicarbonate → 6-chloro-7-cyclopropylmethoxy-9H-beta-carbolin-8-ylamine

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Reaction Steps

6-chloro-7-cyclopropylmethoxy-8-nitro-9H-β-carboline (510 mg, 1.61 mmol) was suspended in 12 ml of methanol and 100 mg of Pd/C (10%) was added. The flask was fitted with a balloon of hydrogen and the reaction mixture was stirred overnight at RT. Upon filtration through a pad of celite and evaporation of the methanol, a dark brown solid was obtained. This residue was suspended in methanol (10 ml) and added, with vigorous stirring, to a solution of saturated NaHCO3 (100 ml). The light brown solid that precipitated out was collected by filtration and dried thoroughly in vacuo to give the desired 6-chloro-7-cyclopropylmethoxy-9H-β-carbolin-8-ylamine (371 mgs, 80% yield). 1H-NMR (300 MHz, methanol-d4): δ 0.36 (m, 2H), 0.61 (m, 2H), 1.37 (m, 1H), 3.88 (d, 2H), 7.58 (s, 1H), 7.96(d, 1H), 8.23 (d, 1H), 8.76 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 2.28 min. MS (M+H+): 288.

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