Methane → HCID 178456120, compound

Participants

Reaction Conditions

Reaction Steps

5.2 g of 2,3-diaminopyridine in 209 g of polyphosphoric acid are heated at 120° C. for 0.5 h. The solution is cooled to 80° C. and 4.6 ml of 2-chloropropionitrile are added. Thereafter, the reaction mixture is heated to 180° C. for 2.5 h. After cooling, the polyphosphoric acid is hydrolysed with 150 ml of water. After reheating to 90° C., charcoal is added under vigorous stirring. Subsequently, the suspension is filtered through a celite pad while still hot (70° C.). The filter cake is rinsed with 100 ml of water and the pH value of the filtrate is adjusted to pH 4 using 9 M aqueous sodium hydroxide solution. The mixture is extracted twice each with 250 ml of ethyl acetate, the combined organic phases are dried using sodium sulfate, concentrated and lyophilised from ethanol/water to give 3.56 g of the title compound as a light brown, amorphous solid. MS: 182.2/184.2 (MH+, 100%/32%. M.p. 132° C. TLC: Rf=0.60 (dichloromethane/methanol 8:1).

Provenance & Evidence