Water → N-(p-fluorobenzyl)isatoic anhydride

Participants

Reaction Steps

Commercially available 2H-3,1-benzoxazine-2,4(1H)-dione (1.0 g, 1.0 eq)) was taken up in N,N-dimethylformamide (15 ml) then treated with portion wise addition of sodium hydride (60% oil dispersion, 0.26 g, 1.05 eq). After stirring 30 minutes, p-fluorobenzyl bromide (1.22 g, 1.05 eq) was dripped in over 5 minutes. The reaction stirred at room temperature for 1 hour. A slurry of yellow solid resulted. Water (15 ml) was added to aid filtration. The solid was collected and recrystallized from ethyl acetate and hexanes (1:3) to afford 1.2 g (73%) of a brown crystalline solid. 1H-NMR (DMSO-d6): δ 8.0-7.9 (m, 1H), 7.8 (t, J=8.7 Hz, 1H), 7.5 (dd, J=8.7, 5.4 Hz, 2H), 7.3-7.0 (m, 4H), 5.3 (s, 2H); LC/MS calc M+Na 294, obs M+Na 294.

Provenance & Evidence