Methanol → HCID 12798059, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,2,3,4-tetrahydro-1,4-ethanocarbazole-2-carboxylic acid methyl ester (13.0 g, 0.05 mole, described in Example 1), potassium carbonate (7.0 g, 0.05 mole), methanol (160 ml) and water (40 ml) was refluxed for 4 hr (oil bath at 90° C.) and stirred at room temperature for 18 hr. The reaction mixture was poured into water (500 ml) and washed with diethyl ether (2×). The aqueous phase was acidified with hydrochloric acid IN (100 ml) and extracted with diethyl ether (3×). Organic layers were washed with a saturated sodium chloride solution, dried and evaporated to dryness to afford the title compound (12 g). Crystallization afforded a total of 7.5 g of title compound: mp 212°-214° C.; NMR (DMSO-d6) δ 1.7 (m, 6H), 2.8 (m, 1H), 3.5 (m, 2H), 6.7-7.5 (m, 4H), 10.9 (s, 1H) and 11.8 (br, 1H); and Anal. Calcd for C15H15O2N: C, 74.66% H, 6.27% N, 5.81% and Found: C, 74.67% H, 6.48% N, 5.80%.

Provenance & Evidence