Benzylamine → Ethyl 1-benzyl-3-cyano-1H-pyrrole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of (2E,4E,6E)-diethyl 3,6-dicyano-2,7-dihydroxyocta-2,4,6-trienedioate (18 g, 58.8 mmol) in N,N-Dimethylformamide (DMF) (100 mL) and Ethyl acetate (100 mL), was treated with benzylamine (15.44 mL, 141 mmol) and the resultant was heated at 95° C. for 3 hours. The dark mixture was concentrated and purified on silica gel (0-70% ethyl acetate/hexanes) to afford ethyl 1-benzyl-3-cyano-1H-pyrrole-2-carboxylate (8.7 g, 34.1 mmol, 60% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.25-7.45 (m, 3H) 7.11-7.16 (m, 2H) 6.84-6.87 (m, 1H) 6.53-6.58 (m, 1H) 5.59 (s, 2H) 4.37 (q, J=7.04 Hz, 2H) 1.40 (t, J=7.13 Hz, 3H); LCMS (m/z) ES+=255 (M+1).

Provenance & Evidence