Benzocaine → HCID 54337669, compound

Participants

Reaction Steps

To a suspension of 5-(1-benzylindol-3-yl)-2,4-pentadienoic acid (0.9 g, 2.9 mmol) in 20 ml of methylene chloride was added dropwise with stirring at room temperature 0.26 ml (0.38 g, 3 mmol) of oxalyl chloride, followed by four drops of N,N-dimethyl-formamide (DMF). The reaction mixture was stirred for an additional 90 min. and concentrated on rotary evaporator. The residue was dissolved in 10 ml of anhydrous methylene chloride and added dropwise to a solution of ethyl p-aminobenzoate (0.44 g, 2.7 mmol) in 5 ml of methylene chloride and 1.3 ml of pyridine. The resulting mixture was stirred at room temperature for 18 hours and washed with saturated aqueous sodium bicarbonate solution and water, dried (MgSO4) and mixture. Purification by a dry column (hexane:ethyl acetate, 2:1) followed by crystallization (acetone-petroleum ether) afforded 250 mg of yellow crystals, m.p. 162-166. MS(EI)=450(M+), 286 (M+--HNC6H4CO2C2H5 ); nmr (CDCl3): δ1.35 (t, J=7 Hz, 3), δ4.28(q, J=7 Hz, 2), δ5.22(s, 2), δ5.95(d, J=15 Hz, 1).

Provenance & Evidence