Hydrochloric Acid → HCID 54435669, compound

Participants

Reaction Steps

This compound was prepared from the product of Example 2 by treatment with sodium carbonate in methanol by a modification of the procedure of Saxena et al (supra). Alternatively, it could be made by esterification of α-acetylamino-3,4-dimethoxycinnamic acid. Thus, 9.62 g of the acid was heated under reflux for 19 hours in 100 mL of methanol containing 1 mL of concentrated hydrochloric acid. After diluting with 500 mL of water, the solution was basified with a 10% aqueous solution of sodium carbonate to a pH of 8-9. The resultant solids were collected by filtration, washed with 3×50 mL of water and dried at the pump. The crude product was further purified by column chromatography on silica gel, eluting with a gradient of methylene chloride/methanol (99:1 thru 96:2). After stripping the solvent from the appropriate fractions, and drying at the pump 2.07 g (21%) of the title compound were obtained; 1HNMR (CDCL3) 7.42 (s, 1H), 7.10 (d, J= 8.5 Hz, 1H), 7.07 (s, 1H), 6.99 (s, 1H), 6.86 (d, J=8.5 Hz, 1H), 3.91 (s, 3H), 3.86 (s, 3H), 3.84 (s, 3H), 2.17 (s, 3H); MP 198°-200° C. Anal. calcd for C14H17NO5 : C, 60.2; H, 6.14; N, 5.02. Found: C, 60.42; H, 5.78; N, 4.53.

Provenance & Evidence