Acetic Acid → 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid (3-methoxy-4-methyl-phenyl)-amide

Participants

Reaction Steps

5,7-Dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester (975 mg) (see Robin D. Allan and Joyce Fong, Aust. J. Chem., Vol. 36, Pp. 1221-1226,1983), 3-metoxy-2-methyl-phenylamine (750 mg) and acetic acid (0.4 ml) were suspended in toluene (30 ml). This mixture was refluxed for one hour under nitrogen. The mixture was cooled to room temperature and the ppt was collected with suction. The ppt was washed with toluene and dichloromethane and dried under reduced pressure to give an orange powder (1.1 g). ESI−MS: m/z 311 (MH+); 1H-NMR (DMSO-d6+triethylamine (1 eq.)): δ2.18 (3H, s), 3.77 (3H, s), 6.60 (1H, d, J=8 Hz), 7.05 (1H, t, J=8 Hz), 7.32 (1H, dd, J=4.5 Hz, J=1 Hz), 7.99 (1H, d, J=8 Hz), 8.50 (1H, d, J=1 Hz), 8.71 (1H, d, J=4.5 Hz), 10.6 (1H, s).

Provenance & Evidence