反应详情

A solution of 3-phenyl-but-2-enoic acid (16.2 g), diphenylphosphoryl azide (27.5 g), and triethylamine (10.1 g) in benzene (100 mL) was stirred for 1 h. After filtration through a silica gel plug washing with benzene and concentration, the residue was dissolved in diphenylmethane (80 mL) and refluxed for 3 h. After cooling to rt, solids were collected through a plug washing with benzene and dried to give 10 g (63%) of the desired 4-methyl-2H-isoquinolin-1-one as a solid. 1H NMR (400 MHz, CD3OD) δ ppm 2.30 (s, 3H), 7.00 (s, 1H), 7.54 (m, 1H), 7.77 (m, 2H), 8.33 (d, J=7.34 Hz, 1H).

1. filtrationAfter filtration through a silica gel plug
2. washwashing with benzene and concentration
3. dissolutionthe residue was dissolved in diphenylmethane (80 mL)
4. temperaturerefluxed for 3 h
5. customsolids were collected through a plug
6. washwashing with benzene
7. customdried