Hydrochloric Acid → 2,7-Dimethylquinolin-6-ol

Participants

Reaction Conditions

Reaction Steps

To 4-amino-2-methylphenol (Aldrich, 5.0 g, 40.6 mmol) was added 6M HCl (100 mL) and heated to 100° C. with stirring. Toluene (30 mL) was added, followed with the slow addition of crotonaldehyde (6.7 mL, 81.2 mmol) at 100° C. The mixture was stirred at 100° C. for 2 additional hours, cooled to room temperature. The water layer was separated, neutralized by NaHCO3 solution. The solid formed was filtered and collected. LCMS-ESI+ (m/z): [M+H]+ calc'd for C11H12NO: 174.2; Found: 174.2.

Provenance & Evidence