Benzoyl chloride → Quinoline-2-carbonitrile

HRID 552037

Reaction equation

HRID 552037 reaction equation
[N+:1]1([O-])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C1C=CC=CC=1.[C-:21]#[N:22].[K+].O1CCOCC1>O>[C:21]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)#[N:22]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 9032Potassium CyanideHCID 15366Quinoline 1-oxideHCID 312751,4-Dioxane

Product 1

HCID 74031Quinoline-2-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of quinoline N-oxide (2g, 13.8 mmol) was added benzoyl chloride (2.6 mL, 22.0 mmol), followed by water (20 mL). Then, a solution of potassium cyanide (3.6 g, 55.1 mmol) in water (80 mL) was added slowly over a period of 15 minutes with vigorous stirring. Dioxane (15 mL) was added to help the solubility. After the mixture was stirred at RT for 2.5 hours, it was extracted with equal volume of dichloromethane three times. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under vacuum. The residue was then purified by flash chromatography with 30% of ethyl acetate in hexane. 2.1 g of product was obtained (yield: 100%).

Workup

  1. extractionit was extracted with equal volume of dichloromethane three times
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under vacuum
  4. customThe residue was then purified by flash chromatography with 30% of ethyl acetate in hexane

Sources & evidence

ORD record
ord-3e56d2022773423686b5868d306e77d7
Source dataset
uspto-grants-2011_05
Patent number
US07951550B2

Linked notes

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