4-Amino-3-hydroxypyridine → N,N-Diethyl-N'-(3-hydroxypyridin-4-yl)methanimidamide

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Reaction Steps

A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C.

Provenance & Evidence