6-Methylquinoline → HCID 11381296, compound

HRID 1988103Notes

Reaction equation

HRID 1988103 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C-:12]#[N:13].[K+].[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>ClCCl.O>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:8]2[C:9]3[C:4](=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=3)[CH:5]=[CH:6][CH:7]2[C:12]#[N:13])=[O:21])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 70596-MethylquinolineHCID 85014-Chlorobenzoyl chlorideHCID 9032Potassium Cyanide

Product 1

HCID 11381296HCID 11381296, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a biphasic mixture of 6-methylquinoline (1.0 g) in dichloromethane (9 mL) and potassium cyanide (1.37 g) in water (4 mL) was added 4-chlorobenzoyl chloride (1.78 mL). The reaction mixture was stirred at ambient conditions overnight. The reaction mixture was then filtered and the filtrate washed successively with water, 1N hydrochloric acid, 1N sodium hydroxide solution and water. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by liquid chromatography (gradient elution of acetonitrile (0.02% trifluoroacetic acid)/water (0.02% trifluoroacetic acid) through a reverse phase C 18 column) to give the titled compound (118 mg product, 5% yield) as a foam. (M+H)+−309.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe filtrate washed successively with water, 1N hydrochloric acid, 1N sodium hydroxide solution and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by liquid chromatography (
  7. washgradient elution of acetonitrile (0.02% trifluoroacetic acid)/water (0.02% trifluoroacetic acid) through a reverse phase C 18 column)

Sources & evidence

ORD record
ord-add70b74925f4479acba719fdba3ffbc
Source dataset
uspto-grants-2009_06
Patent number
US07553967B2

Reaction notes

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