Quinoline → HCID 21219138, compound

HRID 1585569Notes

Reaction equation

HRID 1585569 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]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.C[Si]([C:25]#[N:26])(C)C>[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)Cl>[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([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:25]#[N:26])=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7047QuinolineHCID 678794-Fluorobenzoyl chlorideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 21219138HCID 21219138, compoundYield 150%

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, 39.0 g of 4-fluorobenzoyl chloride, 0.1 g of aluminum chloride, 30.0 g of trimethyl silyl cyanide, and 500 mL of methylene chloride. The title compound (42.0 g) was obtained as a solid, m. p. 111-113° 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 4.

Workup

  1. customThe title compound was prepared by the procedure

Sources & evidence

ORD record
ord-5e72cfb9eb654905965cf787c33a28a4
Source dataset
uspto-grants-1999_08
Patent number
US05939435

Reaction notes

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