Diethyl Ether → HCID 19736594, compound

Participants

Reaction Conditions

Reaction Steps

A solution of phosgene in toluene (36.3 ml×20%) was added dropwise over 30 min to a stirred solution of ethyl-4-chloroanthranilate (10.0 g) and triethylamine (15 ml) in dry tetrahydrofuran at -5° C. The temperature was maintained at -5° C. for 1 h and then allowed to warm to room temperature. After 1 h ether (200 ml) was added and the solution filtered. Removal of solvent under reduced pressure afforded the product as a white solid (11.2 g). δ(CDCl3) 1.39 (3H, t, J=7.5 Hz, CH2CH3), 4.34 (2H, q, J=7.5 Hz, CH2CH3), 7.22 (1H, d, J=CH2CH3, 1.0 Hz, H-6), 7.28 (1H, dd, J=6.5 and 1.0 Hz, H-4), 8.31 (1H, d, J=6.5 Hz, H-3); m/z (EI +) 225.

Provenance & Evidence