3',4'-Dimethoxycinnamic acid → HCID 67395909, compound

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Reaction Steps

To a solution of 1.35 gm (6.5 mmol) of 3-(3,4-dimethoxy-phenyl)-acrylic acid (compound of Example 2; Step 1) in 6 mL of toluene, 1.14 gm (7.0 mmol) of 1,1-carbonyldiimidazole was added lot wise at 25° C. to 30° C. under inert atmosphere. The mass becomes thick and 5 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-hydroxyoctanimidamide (compound of Example 50; 2.1 g, 13.2 mmol) in 5 mL of toluene was added to the above reaction mixture as one lot at 25° C. to 30° C. The reaction mixture was stirred at 25° C. to 30° C. under nitrogen for 12-14 h, followed by stirring at 100° C. to 105° C. for 6-8 h. After completion of the reaction, the reaction 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 organic layers were combined and washed with 10 mL of 1N HCl solution, 10 mL of 5% sodium bicarbonate solution and 10 mL of 10% sodium chloride solution. The organic layer was distilled to obtain a crude residue, which was purified by column chromatography (silica gel, chloroform-methanol) to yield the title compound.

Provenance & Evidence