Ethyl 5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate → ethyl 6-amino-5-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

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Reaction Steps

Ethyl 5-methyl-6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (340 mg, 1.12 mmol) and palladium hydroxide (60 mg) were dissolved in EtOH (50 mL) and stirred for 18 h under H2 (55 psi). The mixture was filtered through Celite and the filtrate was evaporated to give ethyl 6-amino-5-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate as a light tan solid (202 mg, 66%). 1H NMR (CDCl3, 300 MH) δ 6.85-7.02 (m, 2H), 6.43-6.51 (d, 1H, J=7.0 Hz), 4.80 (br. s, 2H), 4.21 (q, 2H, J=6.6 Hz), 3.90 (s, 3H), 3.80-3.88 (m, 2H), 2.75-2.80 (m, 2H), 1.27 (t, 3H, J=7.3 Hz) ppm.

Provenance & Evidence