Quinoline → 5-Benzoylthiophene-2-carbonitrile

HRID 894259Notes

Reaction equation

HRID 894259 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]=1

Participants

3

Reactant 2

HCID 7047QuinolineHCID 2986042-Bromo-5-benzoylthiophene

Product 1

HCID 211624765-Benzoylthiophene-2-carbonitrile

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

  1. customsolids removed by filtration with 15 ml
  2. washof water wash
  3. additionThe combined filtrate and washings were poured into approximately 300 g
  4. extractionextracted into 300 ml
  5. extractionThe ether extract
  6. washwas back-washed with 150 ml
  7. filtrationof water, filtered from insolubles
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-45d3530b5d8748929983593054f55a6d
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

Loading…