Reaction #4029

Reaction equation

hydrochloric acid

N-methylpyrrolidone

2-(p-bromophenyl)-5-octylpyridine

copper (I) cyanide

→

2-(p-cyanophenyl)-5-octylpyridine

Solvents

water

Conditions

Workup

1. 1
   Temperaturethe solution was refluxed for 2 hours
2. 2
   workup.ADDITIONwas added to the mixture solution
3. 3
   Extractionthe organic layer was extracted with chloroform
4. 4
   WashThe extract was washed with a 10% aqueous solution of potassium hydroxide
5. 5
   OtherChloroform was removed by distillation
6. 6
   workup.DISTILLATIONThe residue was distilled under reduced pressure (210° to 220° C./2 mmHg)
7. 7
   Otherrecrystallized from methanol

Procedure

94 ml of N-methylpyrrolidone was added to the 47.6 g (0.138 mol) of the 2-(p-bromophenyl)-5-octylpyridine. Then 19.3 g (0.216 mol) of copper (I) cyanide was added and the solution was refluxed for 2 hours. A mixture of 69 g of iron (II) chloride, 13.8 ml of concentrated hydrochloric acid and 69 ml of water was added to the mixture solution and the organic layer was extracted with chloroform. The extract was washed with a 10% aqueous solution of potassium hydroxide and then three times with water. Chloroform was removed by distillation. The residue was distilled under reduced pressure (210° to 220° C./2 mmHg) and recrystallized from methanol to obtain 33 g (0.1113 mol) of 2-(p-cyanophenyl)-5-octylpyridine.

Source