Ammonia → 4-Amino-6-methoxy-2-(3-methoxyphenyl)quinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-methoxy-2-(3-methoxyphenyl)-4-chloroquinoline (5.90 g, 19.68 mmol) and phenol (20 g) was heated with stirring at 180° C. and ammonia was passed through the reaction mixture during 11 h. Phenol was then removed by steam distillation. The mixture was filtered and the filtrate was basified to pH 8 by adding 8% Na2CO3 aqueous solution. The solid formed was collected by filtration and dried to give the desired 4-amino-6-methoxy-2-(3-methoxyphenyl)quinoline, 5.313 g (96.3%); mp 148-149° C.; 1H NMR (DMSO-d6) δ 3.85, 3.90 (each: 3H, s, OCH3), 6.67 (2H, s, exchangeable, NH2), 7.00 (1H, dd, J=2.9 and 8.1 Hz, ArH), 7.10 (1H, s, ArH), 7.28 (1H, dd, J=2.9 and 8.8 Hz, ArH), 7.40 (1H, t, J=8.1 Hz, ArH), 7.53 (1H, d, J=2.9 Hz, ArH), 7.61 (1H, 1H, d, J=8.1 Hz, ArH), 7.64 (1H, t, J=2.2 Hz, ArH), 7.77 (1H, d, J=8.8 Hz, ArH). Anal. Calcd. for (C17H16N2O2): C, 72.84; H, 5.75; N, 9.99. Found: C, 72.82; H, 5.51; N, 10.12.

Provenance & Evidence