N-methyl-2-pyrrolidone → 5-hydroxy-2,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-2,3-dihydro-3-pyridazinone

Participants

Reaction Conditions

Reaction Steps

To a 20 ml volume two-necked flask, 2,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-203)-(13)-28) (0.30 g), N-methyl-2-pyrrolidone (1.17 ml), and an aqueous solution of sodium hydroxide (0.14 g) in water (0.6 ml) were added under a nitrogen atmosphere, and stirred at 70° C. for 2 hours. The reaction mixture was added to iced water, and washed with ethyl acetate. The pH of the resulting aqueous layer was adjusted to 5 with cold dilute hydrochloric acid under ice-cooling. The precipitated solids were collected by filtration, washed with water, and dried to give 0.18 g of 5-hydroxy-2,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-2,3-dihydro-3-pyridazinone ((1-201)-(12)-10).

Provenance & Evidence