Ammonia → 4-Methylisoquinolin-5-ol

Participants

Reaction Steps

A solution of 4-methyl-5-aminoisoquinoline (869 mg) in concentrated sulfuric acid (8 ml) was added with sodium nitrite (379 mg) with ice cooling and stirring and stirred for 0.5 hours. The reaction mixture was added with water (12 ml) and then stirred at 130° C. for 16 hours. The reaction mixture was neutralized with 28% aqueous ammonia solution and extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to obtain the title compound (559 mg).

Provenance & Evidence