Ethanolamine → 6-Chloro-2-(2-hydroxyethyl)-5-nitroisoquinolin-1(2H)-one

Participants

Reaction Steps

A microwave vial was charged with 6-chloro-5-nitro-1H-isochromen-1-one (1.0 g, 0.00443 mol), ethanolamine (0.401 mL, 0.00665 mol), triethylamine (1.24 mL, 0.00886 mol) and methanol (30 mL, 0.7 mol) and the reaction was subjected to microwave at 100° C. for 1 hour. The reaction was complete in the sense that all the starting material was consumed but the major product formed was the chloro displacement with the amine. The solvent was removed and the residue purified by flash chromatography to obtain the product as a yellow solid. MS m/z=269.4 (M+H). 1H NMR (400 MHz; CDCl3) δ 8.41 (d, J=8.56 Hz, 1H), 7.52 (d, J=8.56 Hz, 1H), 7.33 (d, J=8.4 Hz, 1H), 6.31 (d, J=8.56 Hz, 1H), 4.17 (t, J=44.88 Hz, 2H), 3.99 (t, J=5.11 Hz, 2H), 2.55 (bs, 1H).

Provenance & Evidence