Methanol → HCID 178479499, compound

Participants

Reaction Conditions

Reaction Steps

0.256 g (11.1 mmol) of sodium is added at 22° C. under an argon atmosphere to 40 cm3 of methanol. After complete dissolution, 1 g (10.5 mmol) of guanidine hydrochloride is added. After stirring at 22° C. for 3 hours, the reaction mixture is filtered under an argon atmosphere. The filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is dissolved in 10 cm3 of 1,2-dimethoxyethane. 1 g of 3-chlorocarbonyl-1-(quinol-6-yl)-1H-indole hydrochloride, suspended in 40 cm3 of 1,2-dimethoxyethane, is subsequently added at 22° C. under an argon atmosphere. After stirring at 22° C. for 48 hours and after 2 hours at reflux, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is triturated in 15 cm3 of water. After stirring at 22° C. for 1 hour, a few drops of 10N hydrochloric acid solution are added. After stirring at 22° C. for 12 hours, the suspension is filtered and dried to give 0.52 g of 3-guanidinocarbonyl-1-(quinol-6-yl)-1H-indole hydrochloride in the form of a yellow solid melting at 268° C. IR spectrum (KBr): 3343, 3168, 2174, 1693, 1597, 1543, 1502, 1454, 1236, 1199, 772 and 751 cm−1.

Provenance & Evidence