Benzoyl chloride → 1-benzoyl-6-methoxy-2H-quinoline-2-carbonitrile

HRID 1684536Notes

Reaction equation

HRID 1684536 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[C-:13]#[N:14].[K+].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[C:16]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]1[C:13]#[N:14])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 9032Potassium CyanideHCID 148606-Methoxyquinoline

Product 1

HCID 2304931-benzoyl-6-methoxy-2H-quinoline-2-carbonitrileYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10 g (63 mmol) of 6-methoxyquinoline in 80 ml of dichloromethane is mixed with a solution of 12.4 g (188 mmol) of potassium cyanide, and 14.5 ml (125 mmol) of benzoyl chloride are then added slowly. The mixture is stirred for 18 h, the organic phase is then separated off and the aqueous phase is extracted with dichloromethane. The organic phases are washed with aqueous 5% hydrochloric acid solution and then with water, with aqueous sodium hydroxide solution and again with water, they are dried over sodium sulphate and the solvent is evaporated off under reduced pressure. The oil obtained is crystallized from 95% ethanol. 13.4 g of product are obtained.

Workup

  1. additionare then added slowly
  2. customthe organic phase is then separated off
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. washThe organic phases are washed with aqueous 5% hydrochloric acid solution
  5. dry with materialwith water, with aqueous sodium hydroxide solution and again with water, they are dried over sodium sulphate
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe oil obtained
  8. customis crystallized from 95% ethanol

Sources & evidence

ORD record
ord-5d017520f68340f9b91e14225ca55726
Source dataset
uspto-grants-1997_06
Patent number
US05641785

Reaction notes

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