2-Chloroquinoline → 2-Vinylquinoline

HRID 1850359Notes

Reaction equation

HRID 1850359 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH:12]([Sn](CCCC)(CCCC)CCCC)=[CH2:13]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[CH2:13]

Participants

5

Reactant 2

HCID 119282-ChloroquinolineHCID 81998Tributylvinyltin

Product 1

HCID 698752-VinylquinolineYield 99.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-chloroquinoline (1 g, 6.11 mmol) and vinyl tributyl tin (2.69 mL, 9.17 mmol) in toluene (30 mL) was treated with Pd(PPh3)4 (0.706 g, 0.611 mmol) and heated to reflux for 1.5 h. The reaction mixture was concentrated and the resulting material was purified directly by gradient elution on silica gel (0 to 25% EtOAc in hexanes) to afford the title compound as a colorless oil (941 mg, 99%). All spectral data matched literature values. Fakhfakh, M. A.; Franck, X.; Fournet, A.; Hocquemiller, R.; Figadère, B. Tetrahedron Lett. 2001, 42, 3847. LRMS m/z (M+H) 156.1 found, 156.2 required.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting material was purified directly by gradient elution on silica gel (0 to 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5bd7a1a045db4629a5a83363954ccde8
Source dataset
uspto-grants-2015_02
Patent number
US08957077B2

Reaction notes

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