1,2-Dichloroethane → HCID 131714819, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 4.28 g (0.009 mole) of 2-[2-(diethylamino)ethyl]-5-nitro-2H-[1]benzoselenino[4,3,2-cd]indazol-9-ol, hydrochloride and 0.650 g of 20% palladium on carbon in 100 ml N,N-dimethylformamide is hydrogenated at atmospheric pressure for 13 hours. An additional 0.25 g of catalyst is added and the hydrogenation continues for another 24 hours. The mixture is filtered through a Celite pad and the filtrate is concentrated in vacuo to 4.74 g of a dark orange-brown oil. To this oil is added 2.67 g (0.011 mole) of N-(2-bromoethyl)phthalimide and the mixture is heated under argon in a 110° C. oil bath for 20 hours. To the resulting solid is added 200 ml of 1,2-dichloroethane and 3.3 ml of diisopropylethylamine. The mixture is heated under reflux in an argon atomosphere for two hours, diluted further with dichloromethane, and washed once with a saturated solution of aqueous sodium bicarbonate. The organic layer is separated, dried over sodium sulfate, filtered, and concentrated to a crude solid. The solid is dissolved in dichloromethane and filtered through a small column of Florisil with a 1:9 (v/v) solution of methanol and 1,2-dichloroethane. The effluent is concentrated and the resulting solid is triturated with hot 2-propanol to give 1.98 g of the dried product; mp 203°-205° C.

Provenance & Evidence