Oxalyl chloride → HCID 68853800, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 170 mg (0.83 mmol) of 3-cyanoisopropyloxybenzoic acid in 10 mL of anhydrous CH2Cl2 and 10 μL of DMF was treated with 1.0 mL of oxalyl chloride. The reaction mixture was heated to 50° C. for 10 minutes, cooled to rt and the solvents were removed under reduced pressure. The resulting crude material was dissolved in 10 mL of EtOAc and added in one portion to a vigorously stirring biphasic mixture of 209 mg of 4-bromo-2-methylbenzhydrazide (0.91 mmol), 20 mL of EtOAc, and 20 mL of saturated aqueous solution of sodium bicarbonate. After 30 minutes, the precipitate was collected by filtration and rinsed with 2×10 mL of water and dried in a desiccator overnight. Product (299 mg) was found to be >95% pure by 1H NMR and used in subsequent cyclization step without further purification: 1H NMR (500 MHZ, temp.=50° C., CDCl3) δ 1.55 (d, J=6.5, 6H), 2.51 (s, 3H), 4.78 (sep, J=6.5, 1H), 7.04 (d, J=9.0, 1H), 7.42 (s, 2H), 7.48 (s, 1H), 8.02 (dd, J=9.0, 2.0, 1H), 8.10 (d, J=2.0, 1H), 8.66 (d, J=2.0, 1H), 9.18 (d, J=2.0, 1H).

Provenance & Evidence