(E)-Methyl 2-(2-(dimethylamino)vinyl)-3-nitrobenzoate → 5-nitro-1H-isochromen-1-one
Reaction equation
CN(C)/C=[CH:4]/[C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]>C(OCC)(=O)C>[N+:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:6]2[C:5]=1[CH:4]=[CH:10][O:9][C:7]2=[O:8])([O-:17])=[O:16]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
(E)-Methyl 2-(2-(dimethylamino) vinyl)-3-nitrobenzoate was dissolved in ethyl acetate (200 mL), and silica gel (200 g) was added. The resulting suspension was stirred at room temperature for 1 h. The ethyl acetate solution was filtered off. Silica gel was washed with ethyl acetate (2×150 mL) and the combined organics were evaporated and dried under reduced pressure to yield 5-nitro-1H-isochromen-1-one (4.0 g, 21.0 mmol, 82% after two steps) as a brown solid.
Workup
- addition