Quinoline → HCID 21219136, compound

HRID 1585571Notes

Reaction equation

HRID 1585571 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.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.C[Si]([C:28]#[N:29])(C)C>[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)Cl>[F:11][C:12]([F:23])([F:22])[C:13]1[CH:21]=[CH:20][C:16]([C:17]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]2[C:28]#[N:29])=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7047QuinolineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 21219136HCID 21219136, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the procedure described in step 1 of Example 1 using 13.0 g of quinoline, 32.0 g of 4-trifluoromethylbenzoyl chloride, 0.5 g of aluminum chloride, 14.8 g of trimethyl silyl cyanide, and 500 mL of methylene chloride. Crystallization from diethyl ether/hexane afforded the title compound (28.0 g) as a white solid, m. p. 149-151° 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 6.

Workup

  1. customThe title compound was prepared by the procedure
  2. customCrystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-089f8e1579d740e8ab4e0f397dd53d72
Source dataset
uspto-grants-1999_08
Patent number
US05939435

Reaction notes

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