Methane → HCID 19592905, compound

Participants

Reaction Steps

A mixture of 4-methyl-8-nitroquinoline (2.80 g) and selenium(IV) oxide (1.82 g) in ethanol (45 ml) was refluxed for 4 hours. The mixture was treated with active charcoal and filtered through Celite pad. The filtrate was concentrated in vacuo to afford a brown solid. This residue was dissolved in a mixture of methanol (10 ml) and tetrahydrofuran (10 ml) and cooled in an ice bath. To this solution was added sodium borohydride (170 mg) and stirred at the same temperature for half an hour. To this mixture was added saturated ammonium chloride solution and extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by a flash chromatography on silica gel using methylene chloride then 3% methanol in methylene chloride as the eluent to give a solid. This solid was solidified with diethyl ether to afford 4-hydroxymethyl-8-nitroquinoline (665 mg) as a brown solid.

Provenance & Evidence