Quinoline → 5-Benzoylthiophene-2-carbonitrile
Reaction equation
[C:1]([C:9]1[S:13][C:12](Br)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:15]1C2C(=CC=CC=2)C=C[CH:16]=1>>[C:1]([C:9]1[S:13][C:12]([C:16]#[N:15])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Procedure
5-Benzoyl-2-bromothiophene (8 g., 30 mmoles) and cuprous cyanide (3.2 g., 36 mmoles) were combined in 75 ml. of quinoline and refluxed for 3 hours. The reaction mixture was cooled to room temperature and solids removed by filtration with 15 ml. of quinoline and 15 ml. of water wash. The combined filtrate and washings were poured into approximately 300 g. of ice, acidified with conc. hydrochloric acid and product extracted into 300 ml. of ether. The ether extract was back-washed with 150 ml. of water, filtered from insolubles and concentrated to yield solid 5-benzoyl-2-cyanothiophene (5.7 g., m.p. 85°-89° C., m/e 213).
Workup
- customsolids removed by filtration with 15 ml
- washof water wash
- additionThe combined filtrate and washings were poured into approximately 300 g