Benzenepropanoyl chloride → HCID 3615712, compound

Participants

Reaction Steps

2-Amino-5-bromobenzoic acid (2.0 g, 9.3 mmol, 1.8 equiv) in ether (50 mL) was treated with hydrocinnamoyl chloride (760 uL, 0.51 mmol, 1.0 equiv) and stirred overnight. The solution was filtered and washed sparingly with ether. The filtrate, upon concentration, gave a white amorphous powder which was recrystallized from ethanol/water to give fine yellowish needles of 5-bromo-2-(3-phenylpropanamido)benzoic acid (1.58 g, 4.5 mmol, 89%). This material (1.58 g, 4.5 mmol, 1.0 equiv) was added to acetic anhydride (8 mL) and heated to 100° C. for 30 min. to dissolve all the material, then 160° C. until ca. 20% of the volume had distilled. The reaction mixture was then concentrated in vacuo to provide 6-bromo-2-phenethyl-benzo[3,1]oxazin-4-one as a yellowish waxy solid.

Provenance & Evidence