Hydrochloric Acid → HCID 9927383, compound

Participants

Reaction Steps

Piperidine (0.39 mL, 4.0 mmol) was added to a suspension of 3,4-dimethoxybenzaldehyde (0.66 g, 4.0 mmol) and 4-[(carboxyacetyl)amino]benzoic acid (0.74 g, 3.3 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 1 M HCl. The crude product was recrystallised from EtOH providing (E)-4-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.58 g, 53%) as a yellow crystalline solid; mp 258-259° C., lit. [24] 267-269° C.; δH (400 MHz, DMSO-d6) 3.80 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 6.72 (d, J=15.6 Hz, 1H, CH═CHCO), 7.01 (d, J5′,6′=8.2 Hz, 1H, H5′), 7.20 (d, J5′,6′=8.2 Hz, 1H, H6′), 7.22 (s, 1H, H2′), 7.56 (d, J=15.6 Hz, 1H, CH═CHCO), 7.80 (d, J2,3=J5,6=8.4 Hz, 2H, H3, H5), 7.90 (d, J2,3=J5,6=8.4 Hz, 1H, H2, H6), 10.43 (s, 1H, NH), 12.68 (br s, 1H, CO2H).

Provenance & Evidence