Ammonia → 4'-Cyano-biphenyl-4-acetic acid

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Reaction Steps

The compound (840 mg) obtained in the above (2) is dissolved in DMF (7 ml), and thereto are added pyridine (10 μl) and cuprous cyanide (I) (410 mg), and the mixture is refluxed with stirring for 8 hours. To the mixture is further added cuprous cyanide (I) (410 mg), and the mixture is refluxed with stirring for 7.5 hours. After cooling, to the mixture is added a mixture of conc. aqueous ammonia (5 ml) and water (60 ml), and the precipitates are removed by filtration. The filtrate is concentrated under reduced pressure, and the pH value of the residue is adjusted to pH 11 with 1N aqueous sodium hydroxide solution, and washed twice with ether. The pH value of the residue is adjusted to pH 1 with conc. hydrochloric acid, and extracted three times with ethyl acetate. The organic layer is washed with a saturated brine, and dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (654 mg).

Provenance & Evidence