3-ethyl-2,3-dihydro-1H-indole → HCID 19029095, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,6-dimethyl-4-(trifluoromethanesulphonyloxy)-2-pyridone (1.5 g, 5.5 mM) and 3-ethylindoline (1.22 g, 83 mM) was heated at an external temperature of 150° C. under argon for 3 hours. The solution was cooled. The residue was triturated with acetone to afford a solid which was collected by filtration. This solid was washed with acetone to give 1,6-dimethyl-4-(3-ethylindolin-1-yl)-2-pyridone as the hemi-trifluoromethylsulphonate salt; (1.76 g, 62% yield); m.p. 174°-175° C.; microanalysis, found C, 60.2; H, 6.0: N, 8.0%; C18H21N2. 0.5CF3SO3H requires: C, 60.1; H, 5.9; N, 8.0%: NMR (DMSOd6); 0.9-1.0(3H, t, CH2CH3), 1.4-1.6(1H, m, CHEt), 1.70-1.9(1H, m, CHEt), 2.44(3H, s, CH3), 3.25-3.4(1H, m, indoline H), 3.5(3H, s, +NCH3), 3.6-3.7(1H, m, indoline H), 4.05-4.15(1H, m, indoline H), 6.2(1H, d, pyridine CH), 6.6(1H, d, pyridine CH), 6.9-7.05(1H, t, aromatic), 7.15-7.4(3H, m, aromatic).

Provenance & Evidence