Water → HCID 67395719, compound

Participants

Reaction Steps

3-(3,4-Dimethoxy-phenyl)-acrylic acid (compound of Example 2, Method A, Step 1; 2.0 g, 9.6 mmol) was dissolved in DMF (20 mL) to which 1,1′-carbonyldiimidazole (CDI) (1.71 g, 10.56 mmol) was added and the reaction mixture was stirred at room temperature. At the end of 3 h, N-hydroxy-2-phenyl-acetamidine (1.58 g, 10.56 mmol) was added and the reaction mixture was stirred at room temperature for 8 h. After the completion of the reaction, additional CD (1.71 g, 10.56 mmol) was added and the reaction mixture was refluxed at 110° C. to 120° C. for 8 h to effect cyclodehydration. DMF was evaporated and the residue obtained was cooled to room temperature followed by addition of water (15 mL). The resulting mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (2×10 mL) and brine (10 mL). The organic phase obtained was dried over anhydrous sodium sulfate and concentrated to afford the title compound.

Provenance & Evidence