1,3-Propanediamine → HCID 13687221, compound

Participants

Reaction Conditions

Reaction Steps

Under a slow stream of argon gas, a mixture of 19.4 g (0.035 mol) of crude 5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7,10-bis(phenylmethoxy)anthra[1,9-cd]-pyrazol-6(2H)-one (2) and 29 ml (25.8 g, 0.35 mol) of 1,3-propanediamine was stirred at 130° C. for 3.5 hours, allowed to cool and triturated with water and 2-propanol. The solid was collected, washed successively with water, 2-propanol and ethanol, and dried under vacuum at 40° C. to give 16.9 g of crude product. Chromatography over 1 kg of silica gel (230-400 mesh) with a mixture of methanol:dichloromethane:triethylamine in the following ratios: 20:79:1, then 30:69:1, and finally 40:59:1 provided 11 g. This material was recrystallized from pyridine, washed with 2-propanol, and dried under vacuum overnight at 60° C. to afford 9.7 g (46.8%) of 3, mp 204°-206° C.

Provenance & Evidence