Sodium Bicarbonate → 6-Chloro-7-methoxy-9h-pyrido[3,4-b]indol-8-amine

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Reaction Steps

6-chloro-7-methoxy-8-nitro-9H-β-carboline (510 mg, 1.84 mmol) was suspended in 50 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 (15 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 product (512 mg, quantitative yield). 1H-NMR (300 MHz, methanol-d4): 63.90 (s, 3H), 7.63 (s, 1H), 8.11 (d, 1H), 8.27 (d, 1H), 8.84 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.12 min.

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