Methanol → 6-Methoxy-7-(3-chloropropoxy)quinazolin-4-one

Participants

Reaction Conditions

Reaction Steps

In a 1,000 mL volume stainless pressure-resistant vessel equipped with a stirrer, a thermometer and a pressure gauge were placed 161.5 g (0.59 mol) of methyl 5-methoxy-4-(3-chloropropoxy)anthranilate, 156.5 g (1.48 mol) of methyl orthoformate, 113.7 g (1.48 mol) of ammonium acetate, and 300 mL of methanol. The vessel was closed, and the reaction was carried out at 90-95° C. for 8 hours. The pressure in the vessel was 0.1-0.3 MPa (gauge pressure). After the reaction was complete, 600 mL of water was added to the reaction mixture. The aqueous reaction mixture was stirred at 0-10° C. for one hour, to precipitate a crystalline product. The crystalline product was collected by filtration, washed with 600 mL of water, and dried at 60° C. under reduced pressure, to give 152.8 g (isolated yield: 94%) of 6-methoxy-7-(3-chloropropoxy)quinazolin-4-one as a white crystalline product.

Provenance & Evidence