3',4'-Dimethoxycinnamic acid → HCID 67396892, compound

Participants

Reaction Steps

To a solution of 0.547 g (2.6 mmol) of 3-(3,4-dimethoxy-phenyl)-acrylic acid (compound of Example 2; Step 1) in 8 mL of toluene, 0.46 g (2.8 mmol) of 1,1-carbonyldiimidazole was added in portions at 25° C. to 30° C. under inert atmosphere. To the thick mixture, 1 mL of toluene was added and the resulting mixture was stirred at 25° C. to 30° C. for 60 to 90 min. A solution of N-hydroxy-decanimidamide (compound of Example 32; 1.0 g, 5.3 mmol) in 3 mL of toluene was added to the above reaction mixture at 25° C. to 30° C. The reaction mixture was stirred at 25° C. to 30° C. under nitrogen for 12-14 h and further at 100° C. to 105° C. for 6-8 h. After completion of the reaction, the mixture was cooled to 25° C. to 30° C. and quenched with 10 mL of chilled water under stirring at 25° C. to 30° C. The organic layer was separated, and the aqueous layer was washed with 5 mL of toluene. The combined organic layers was washed with 5 mL of 1N HCl solution, 5 of 5% sodium bicarbonate solution and 5 mL of 10% sodium chloride solution. The organic layer was distilled to yield a crude material, which was purified by column chromatography (silica gel, chloroform-methanol) to yield the title compound.

Provenance & Evidence