反应详情

A stirred suspension of 1-(4-fluoro-phenyl)-3-oxo-1,3-dihydro-isobenzofuran-5-carboxylic acid (1 g, 3.7 mmol) in thionyl chloride (25 mL) was heated at reflux for 25 min, during which time the solid dissolved. The thionyl chloride was then evaporated, and the residue was dissolved in toluene, and again evaporated. The residue was dissolved in toluene (15 mL) and was treated with a solution of ammonia in ether and a heavy precipitate formed. The mixture was stirred overnight, diluted with toluene and aqueous ammonia solution, and filtered. The residue was dried to give the title compound as a white solid (0.80 g, 80%). 1H NMR (d6-DMSO): δ 6.81 (s, 1H), 7.25 (t, 2H), 7.40 (dd, 2H), 7.54 (d, 1H), 7.59 (bs, 1H), 8.24 (bs, 1H), 8.24 (dd, 1H), 8.42 (s, 1H).

1. temperaturewas heated
2. temperatureat reflux for 25 min, during which time the solid
3. dissolutiondissolved
4. customThe thionyl chloride was then evaporated
5. dissolutionthe residue was dissolved in toluene
6. customagain evaporated
7. dissolutionThe residue was dissolved in toluene (15 mL)
8. additionwas treated with a solution of ammonia in ether
9. customa heavy precipitate formed
10. filtrationfiltered
11. customThe residue was dried