Chloroacetonitrile → methyl 2-(chloromethyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of dimethyl 2-aminoterephthalate (1.70 g, 8.1 mmol) in 4.0 M hydrochloric acid in 1,4-dioxane (20 mL) was added chloroacetonitrile (0.88 mL, 14 mmol). The reaction mixture was heated to 50° C. and stirred for 3 h. The mixture was then cooled to rt, concentrated and the residue was twice co-evaporated with toluene. Water was added and the solid was filtered to afford methyl 2-(chloromethyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (1.8 g, 88%). LC-MS: (FA) ES+ 253; 1H NMR (400 MHz, DMSO) δ 12.81 (s, 1H), 8.23 (d, J=8.2 Hz, 1H), 8.14 (d, J=1.1 Hz, 1H), 8.02 (dd, J=8.2, 1.6 Hz, 1H), 4.57 (s, 2H), 3.92 (s, 3H).

Provenance & Evidence