2-Chloroquinoline → 2,2'-Biquinoline

HRID 2301692Notes

Reaction equation

HRID 2301692 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.[OH-].[Na+]>O.CO.[Pd]>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 2

HCID 119282-ChloroquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 84122,2'-BiquinolineYield 43.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
82.5 °C

Procedure

5.00 g of 2-chloroquinoline and 1.80 g of sodium hydroxide are dissolved in a mixture of 20 ml of water and 16 ml of methanol. Following the addition of 1.5 g of palladium (10% by weight on activated carbon) as catalyst, the mixture is stirred for 24 h at 80-85° C. at 0.1 MPa. Then, following cooling, the catalyst and the precipitated product are filtered off. Extraction of the catalyst gives 1.7 g of 2,2′-biquinoline (43% yield). According to 1H NMR, the crude product has a purity of about 98%. CAS Registry Number: 119-91-5.

Workup

  1. temperatureThen, following cooling
  2. filtrationthe catalyst and the precipitated product are filtered off
  3. extractionExtraction of the catalyst

Sources & evidence

ORD record
ord-08ffef62082a4a439a89a092a712536d
Source dataset
uspto-grants-2002_12
Patent number
US06500956B1

Reaction notes

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