Water → Ethyl 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate

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Reaction Steps

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-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 h under reflux. The medium is cooled and 350 ml of dichloromethane and 100 ml of water are added. The organic phase is decanted off, washed with a saturated aqueous sodium hydrogen carbonate solution, then with water, dried over sodium sulphate, filtered, concentrated under reduced pressure and the residue purified by chromatography on a silica gel column.

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