Ammonium Hydroxide → HCID 23289880, compound

Participants

Reaction Conditions

Reaction Steps

Bromine (1.0 ml, 19.4 mmol) was added to a suspension of ethyl 4-(3-amino-8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-1-piperidine-carboxylate (1.5 g, 3.75 mmol) in hydrobromic acid (150 ml) at 0° C. for 10 minutes. Sodium nitrite (0.7 g, 10.14 mmol) in water (5 ml) was added at 0° C., and the mixture was stirred at 0° C. for 1 hour and then at 20° C. for 2 hours. The reaction mixture was poured onto ice (200 g), basified with concentrated ammonium hydroxide and extracted with ethyl acetate (500 ml). The organic layer was washed with water (300 ml), dried (MgSO4), filtered and evaporated, yielding a crude product which was chromatographed on silica gel and eluted with 30%ethylacetate/hexanes. The product was recrystallized from ether to afford a white powder, ethyl 4-(3-bromo-8-chloro-5,11-dihydro[1]benz-oxepino[4,3-b]pyridin-11-ylidene)-1-piperidine-carboxylate (1.0 g, 58%), m.p. 148-149° C. MS (CI, M+H)=463; anal.: found: C, 53.92; H, 4.16; N, 6.18; C21H20BrClN2O3 requires: C, 54.38; H, 4.34; N, 6.04.

Provenance & Evidence