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

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Reaction Steps

6-Nitro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (250 mg, 0.99 mmol) was dissolved in CH2Cl2 (2.5 mL) with sat. aq. K2CO3. Ethylchloroformate (130 mg, 1.2 mmol) was added at 0° C. The reaction was brought to room temperature and stirred for 15 h. The layers were separated and the aqueous layer was extracted with CHCl3 (3×5 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and evaporated affording ethyl-6-nitro-1,3,4,5-tetrhydro-2H-pyrido[4,3-b]indole-2-carboxylate as an orange semi-solid (160 mg, 56%). 1H NMR (CDCl3, 300 MHz) δ 8.17 (d, 1H, J=8.1 Hz), 7.78 (d, 1H, J=7.6 Hz), 3.19 (t, 1H, J=8.1 Hz), 4.73 (s, 2H), 4.18-4.23 (m, 4H), 2.91-2.98 (m, 2H), 1.30-1.39 (t, 3H, J=6.9 Hz) ppm.

Provenance & Evidence