Water → Ethyl 7-(4-carbamoylphenoxy)-6-chlorochroman-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of isobutyl nitrite (3.92 g, 15.2 mmol) in DMF (100 mL) at 66° C. was added a solution of ethyl 7-(2-amino-4-carbamoylphenoxy)-6-chlorochroman-4-carboxylate (5.94 g, 15.2 mmol) in DMF (30 mL) dropwise over 14 minutes. The temperature rose to 70° C. during the addition and gas began to evolve. After 37 minutes of stirring at 68-69° C. the resulting solution was cooled to ambient temperature and poured into a reparatory funnel containing water (1500 mL). The resulting mixture was extracted with ethyl acetate (250 mL) and the organic layer was washed with 1M HCl, and brine, dried over sodium sulfate and concentrated to give 5.39 g of brown solid. The solid was triturated with ether and filtered to provide the desired product (4.86 g, 85%).

Provenance & Evidence