Cyclopropylamine → HCID 10517385, compound

Participants

Reaction Steps

Cyclopropylamine (10 mL) was added to a stirred solution of benz[d]indeno[1,2-b]pyran-5,11-dione (2) (0.28 g, 1.1 mmol) in CHCl3 (10 mL). The red solution stirred overnight before CHCl3 (50 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 red solid (0.3 g, 91%): mp 206-208° C.; IR (thin film) 3751, 1665, 1500, 1420, 1311, 1083, 950 cm−1; 1H NMR (CDCl3, 300 MHz) δ8.62 (d, 1H, J=7.7 Hz), 8.29 (d, 1H, J=8.4 Hz), 7.88 (d, 1H, J=7.0 Hz), 7.69 (td, 1H, J=6.9, 1.2 Hz), 7.59 (dd, 1H, J=6.1, 1.3 Hz), 7.40 (m, 3H), 3.37 (m, 1H), 1.45 (q, 2H, J=6.8 Hz), 0.99 (m, 2H); CIMS m/z (relative intensity) 288 (MH−, 100). Anal. Calcd for C19H13NO2: C, H, N.

Provenance & Evidence