3-chloro-N-(4-hydroxyphenyl)propanamide → 6-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-N-(4-hydroxyphenyl)propanamide (122 g, 0.61 mol) and AlCl3 (327 g, 2.45 mol) were slowly heated with vigorous stirring at 180° C. (a thick melt formed) and after 5 hours the liquid was poured over ice. The solids were collected by filtration, washed with water, and recrystallized from MeOH to afford 6-hydroxy-3,4-dihydro-2(1 H)-quinolinone (80 g, 40% yield). 1H NMR (400 MHz, DMSO) δ, 2.32-2.36 (m, 2 H), 2.74 (t, 2 H, J=7.2 Hz), 6.50 (m, 1 H), 6.54 (d, 1 H, J=2.8 Hz), 662(d, 1 H, J=8.4 Hz), 9.00 (br, 1 H), 9.78 (br, 1 H).

Provenance & Evidence