4-Chlorobenzylamine → HCID 10295685, compound

Participants

Reaction Conditions

Reaction Steps

4-Chlorobenzylamine (110 μL) and sodium methoxide (25 mg) are added to a solution of ethyl 8-(3-hydroxyprop-1-ynyl)-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate (Preparation 14, 153 mg) in methanol (12 mL). The reaction is warmed to 50° C. for 48 hours. The reaction mixture is cooled in a freezer and the resulting white precipitate is filtered and washed with cold methanol, hexane, and ether to give 150 mg of the title compound as white crystals. Physical characteristics: M.p. 228° C. (dec); 1H NMR (DMSO-d6) δ10.43, 8.98, 7.90, 7.66, 7.40, 5.39, 4.54, 4.34, 3.44, 1.66; IR (diffuse reflectance) 2226, 1907, 1646, 1618, 1568, 1538, 1510, 1493, 1434, 1318, 1307, 1223, 1033, 1012, 808 cm−1; MS (EI) m/z 420 (M+); HRMS (FAB) 421.1332 (C24H21ClN2O3+H).

Provenance & Evidence