Propylamine → 6-Propyl-5H-indeno(1,2-c)isoquinoline-5,11(6H)-dione

Participants

Reaction Steps

Propylamine (0.3 mL, 3 mmol) was added to a stirred solution of benz[d]indeno[1,2-b]pyran-5,11-dione (2) (0.49 g mmol) in CHCl3 (10 mL). The red solution stirred overnight before CHCl3 (75 mL) was added and the mixture washed with H2O (3×20 mL) and brine (1×20 mL), dried (MgSO4), and concentrated under reduced pressure to give a yellow-orange solid (0.32 g, 55%): mp 166-167° C.; IR (neat) 2967, 1660, 1502, 1427, 1317, 1193, 959 cm−1; 1H NMR (CDCl3, 300 MHz) δ8.69 (d, 1H, J=8.0 Hz), 8.33 (d, 1H, J=9.0 Hz), 7.70 (td, 1H, J=9.0, 3.0 Hz), 7.62 (d, 1H, J=6.2 Hz), 7.40 (m, 4H), 4.46 (t, 2H, J=8.0 Hz), 1.92 (m, 2H), 1.12 (t, 3H, J=7.4 Hz); CIMS m/z (relative intensity) 290 (MH+, 100). Anal. Calcd for C19H15NO2: C, H, N.

Provenance & Evidence