6-chloro-4-methyl-8-nitro-9H-beta-carboline → 6-chloro-4-methyl-9H-beta-carbolin-8-ylamine

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Reaction Steps

A solution of 6-chloro-4-methyl-8-nitro-9H-β-carboline (80 mg, 0.31 mmol) in MeOH (10 ml) was stirred at RT. Platinum (10% wt. on carbon, 24 mg) catalyst was added thereto and the reaction vessel was capped and vacuum purged 3 times with argon, followed similarly by hydrogen. The reaction mixture was stirred 1.5 hr under 1 atm hydrogen, then vacuum purged with argon, diluted with DCM (10 ml) and filtered through a 0.2 μM syringe filter. The filtrate was concentrated to yield 6-chloro-4-methyl-9H-β-carbolin-8-ylamine (67 mg) as a light brown oil. 1H-NMR (300 MHz, DMSO-d6): δ 9.04 (s, 1); 8.29 (s, 1); 7.74 (d, 1); 7.10 (d, 1); 2.98 (s, 3). NH4OAc standard conditions. DAD Rf=1.89 min. M+H=231.

Provenance & Evidence