Hydrochloric Acid → HCID 59463458, compound

Participants

Reaction Conditions

Reaction Steps

As depicted in Scheme 35 below, 2-phenyl-4,5-dihydro-furo[3,2-c]pyridine-6-carboxylic acid (0.015 mol) is added in portions to a mixture of sodium hydride (60% dispersion in mineral oil, 0.045 mol) in anhydrous DMF (35 ml) under a nitrogen stream at 0° C. After 15 minutes phenylacetyl disulfide (0.02 mol) is added portion-wise, and the reaction is then heated to 50° C. and kept at that temperature overnight. The reaction mixture is then cooled to room temperature and poured onto crushed ice, turned acidic with 2N HCl, and extracted with ethyl acetate. The organic phase is separated, washed with brine, and dried over Na2SO4. The solvent is evaporated under reduced pressure and the obtained residue is triturated with hexane and filtered. The obtained crude residue is then refluxed in the presence of HCl 6N and water to give 7-mercapto-2-phenyl-4,5-dihydro-furo[3,2-c]pyridine-6-carboxylic acid.

Provenance & Evidence