反应详情

4 ml (40.6 mmol) of phenylhydrazine are added at room temperature to a solution of 4.6 g (13.6 mmol) of ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-α-oxo-1H-indole-3-acetate in 120 ml of acetic acid. The reaction mixture is stirred for 30 min at room temperature and then for 4 hours at reflux. The mixture is cooled and 350 ml of dichloromethane and 100 ml of water are added. The organic phase is separated by settling, washed with a saturated aqueous sodium hydrogencarbonate solution and then with water, dried over sodium sulphate, filtered and concentrated under reduced pressure and the residue is purified by chromatography on a column of silica gel. 4.1 g (10.7 mmol) of product are isolated.

1. temperaturefor 4 hours at reflux
2. temperatureThe mixture is cooled
3. customThe organic phase is separated
4. washwashed with a saturated aqueous sodium hydrogencarbonate solution
5. dry with materialwith water, dried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customthe residue is purified by chromatography on a column of silica gel