Hydrogen Bromide → HCID 13050889, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4.91 gm. (20 mmoles) of B in 270 ml. of acetic acid and 75 ml. of ether, cooled to 10° C., was added gaseous HBr in excess. A solution of 3.4 gm. (21 mmoles) of bromine in 75 ml. acetic acid was added over 75 min. The resulting mixture was stirred for 1 hour at 22° C., evaporated and the residue stirred with 150 ml. of 10% NaHCO3. The aqueous suspension was extracted with 3×200 mls. of CHCl3 and after drying and evaporation of the organic extracts there was obtained 6.57 gm. of crude 6-bromo-acetyl-2-ethoxy-4-methoxy quinoline. This material was dissolved in 150 ml. of dimethylformamide and to the solution was added a solution of 1.95 gm. (30 mmoles) of sodium azide in 35 ml. of H2O. The solution temperature rose from 22° C. to 35° C. and after 105 minutes had fallen back to 25° C. The mixture was diluted with 1500 ml. of water and extracted with 3×300 ml. of CHCl3. After washing the organic extracts with water (3×200 ml.), drying and evaporation, there was obtained 5.95 gm. of crude solid. This was dissolved in 75 ml. of ethyl acetate, 50 ml. of hexane was added, and after refrigeration and filtration, there was obtained 4.88 gm. (85%) of c, m.p. 129°-132° C.

Provenance & Evidence