Sulfuric Acid → 3-(Methoxymethyl)-8-quinolinol

Participants

Reaction Conditions

Reaction Steps

A solution of methanol and sulfuric acid (10.0 g, 0.1 mol) is heated to 65° C., treated with o-aminophenol (4.36 g, 0.04 mol) and o-nitrophenol (2.78 g, 0.02 mol), heated to 70° C., treated with methoxymethacrolein (6.0 g, 0.06 mol) over 40 minutes at 85° to 90° C. and diluted with water. The aqueous mixture is adjusted to about pH 2 with 50% sodium hydroxide solution and filtered. The filtrate is adjusted to about pH 7 with 50% sodium hydroxide solution and extracted with chloroform. The combined organic extracts are concentrated in vacuo to give the title product as a solid which is identified by 1H and 13CNMR spectral analyses.

Provenance & Evidence