Xanthine → Hypoxanthine

Participants

Reaction Steps

2.18 g (4.5 mM) of xanthine (B.) and 2.6 g of Raney-nickel (treated with 0.1% aqueous acetic acid) were refluxed in 30 ml of 1-propanol for 2.5 hr. The nickel was filtered off and the solution evaporated in vacuo to dryness. The residue was dissolved in 40 ml of ethyl acetate and extracted with sodium bicarbonate solution. The formed solid is filtered off and the organic phase evaporated in vacuo to dryness (1.95 g). A dichloromethane solution, comprising 2% of methanol, was purified on 19 g of silicagel in a column. Crystallization from ethyl acetate gave 1.37 g (67.2%) of hypoxanthine with mp 159-161° C., a second crop gave 0.4 g (2.0%) of hypoxanthine.

Provenance & Evidence