Quinoline → 1-Benzoyl-1,2-dihydroquinaldonitrile

HRID 1585567Notes

Reaction equation

HRID 1585567 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[Si]([C:24]#[N:25])(C)C>[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)Cl>[C:11]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]1[C:24]#[N:25])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7047QuinolineHCID 7412Benzoyl chlorideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 262191-Benzoyl-1,2-dihydroquinaldonitrileYield 66.7%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of quinoline (19.35 g), benzoyl chloride (28.1 g), aluminum chloride (1.0 g) and methylene chloride (500 mL) was stirred at ambient temperature for 10 minutes. Trimethyl silyl cyanide (20.0 g) was added dropwise. The stirring was continued for 4 hours. The mixture was washed twice with 1N HCl (500 mL) then with water (500 mL). The organic phase was dried over anhydrous magnesium sulfate then evaporated to dryness. The title compound (26.0 g) was obtained as a white solid, m.p. 153-154° C. This product was used for the preparation of the title compound described in step 2, and for preparation of the title compound described in Example 2.

Workup

  1. waitThe stirring was continued for 4 hours
  2. washThe mixture was washed twice with 1N HCl (500 mL)
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. customthen evaporated to dryness

Sources & evidence

ORD record
ord-eb95373b96cf4552b00d9493dff94b4b
Source dataset
uspto-grants-1999_08
Patent number
US05939435

Reaction notes

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