Ammonia → HCID 67288320, compound

Participants

Reaction Steps

4-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation A; 150 mg, 0.365 mmol) was diluted with DCM (1.5 mL) followed by the addition of oxalyl chloride in DCM (2M) (201 μl, 0.401 mmol) and DMF (1 drop). Ammonia (6.21 mg, 0.365 mmol) was bubbled in for 10 minutes. The reaction was placed under nitrogen and stirred for 3 hours. The reaction was diluted with ethyl acetate and washed with water. The organic layer was concentrated, loaded onto silica gel and eluted with neat ethyl acetate to yield ethyl 7-(4-carbamoylphenoxy)-6,8-dichlorochroman-4-carboxylate (120 mg, 0.293 mmol, 80.2% yield) as a white solid.

Provenance & Evidence