4-(2-(Pyrrolidin-1-yl)ethyl)aniline → 4-{[4-(2-Pyrrolidin-1-yl-ethyl)-phenylamino]-methylene}-1,4-dihydro-2H-isoquinolin-3-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.400 g (1.98 mmol) of (4E)-4-[(dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone and 0.414 g (2.18 mmol) of 4-(2-Pyrrolidin-1-yl-ethyl)-phenylamine in 4 mL of PhCH3 is heated at 110° C. for 2.5 h. The reaction is placed in a freezer and the precipitated material is collected, washed with cold PhCH3(2×) and Et2O and dried in vacuo to give 0.280 g (41%) of gold crystals: mp 169-173° C. (dec); 1H NMR (DMSO-d6) δ 11.4 (d, 1H, J=11.8 Hz), 8.01 (d, 1H, J=11.8 Hz), 7.63 (m, 2H), 7.16 (s, 4H), 7.07 (m, 2H), 4.40 (s, 2H), 2.60 (m, 4H), 2.50 (m, 2H), 1.67 (s (br), 4H); HRMS (ESI) m/e calcd for C22H25N3O 348.20704. found 348.20588 (M+H)+1.

Provenance & Evidence