Triethylamine → HCID 10591700, compound

Participants

Reaction Steps

Triethylamine (2.7 mL, 19.4 mmol) was added to a stirred solution of glycine methyl ester hydrochloride (1.57 g, 12.5 mmol) in chloroform (30 mL). After 1 h, benz[d]indeno[1,2-b]pyran-5,11-dione (2) (1.24 g, 5.0 mmol) was added to the mixture. The red mixture stirred an additional 4 h before CHCl3 (100 mL) was added and the mixture washed with H2O (3×50 mL) and brine (1×50 mL), dried (MgSO4), and concentrated under reduced pressure to give an orange-red solid (1.48 g, 92%): mp 248-251° C.; IR (thin film) 2956, 1735, 1667, 1609, 1502, 1426, 1227, 981 cm−1; 1H NMR (CDCl3, 300 MHz) δ8.68 (d, 1H, J=8.0 Hz), 8.32 (d, 1H, J=8.2 Hz), 7.73 (td, 1H, J=7.1, 1.3 Hz), 7.61 (m, 1H), 7.47 (td, 1H, J=7.1, 1.1 Hz), 7.37 (m, 2H), 7.26 (m, 1H), 5.34 (s, 2H), 3.79 (s, 3H); CIMS m/z (relative intensity) 320 (MH+, 100). Anal. Calcd for C19H13NO4: C, H, N.

Provenance & Evidence