Hydrochloric Acid → HCID 19386776, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrate (2.0 mmol) in water (1 ml) was slowly added to a stirred suspension of 3,4-diallyloxy-6-aminobenzoic acid (1.8 mmol) in a 2N aqueous solution of hydrochloric acid (5 ml) at 0° C. Water (10 ml) was added and the reaction mixture stirred for 30 minutes. The pH of the mixture was adjusted to pH8 by the addition of solid potassium carbonate. A solution of copper (I) cyanate was prepared by dissolving copper (I) chloride (2.25 mmol) in a solution of sodium cyanate (6.3 mmol) in water (5 ml). This was added to the rection mixture. The resulting mixture was slowly warmed to 50° C. and stirred for 20 minutes. The mixture was then heated on a steam bath for 20 minutes and acidified with a 5N aqueous solution of hydrochloric acid. This solution was extracted with ethyl acetate. The organic phase was washed with a 5N aqueous solution of hydrochloric acid and a saturated aqueous solution of sodium chloride. The organic phase was then extracted with a saturated aqueous solution of sodium hydrogen carbonate. The aqueous phase was acidified and extracted with ethyl acetate. This organic phase was washed with a saturated aqueous solution of sodium chloride and dried (MgSO4). The solvent was evaporated to give 3,4-diallyloxy-6-cyanobenzoic acid as a light orange solid. NMR (DMSO-d6): 4.73(m,4H); 5.35(m,4H); 6.04(m,2H); 7.48(s,1H); 7.57(s,1H): M/S CI (M+H)+= 260.

Provenance & Evidence