2-Chloroquinoline → 2-Cyclopentylquinoline

Temperature

0 °C

To a solution of 2-chloroquinoline (8.2 g, 50 mmol) and [1,2-bis(diphenylphosphino)-ethane]dichloronickel(II) (200 mg, 0.38 mmol) in diethyl ether (20 ml) cooled in a ice/methanol bath was added cyclopentylmagnesium bromide (2 M solution in diethyl ether; 25.5 ml, 51 mmol) over a period of 15 minutes. The resulting brown solution was then stirred for 30 minutes, the ice bath removed and the mixture stirred for a further 10 minutes. The reaction mixture was then re-cooled to 0° C. and a saturated ammonium chloride solution (40 ml) added slowly. The resulting reaction mixture was poured into a separating funnel and further diluted with diethyl ether (60 ml) and saturated ammonium chloride solution (60 ml). The organics were separated and the aqueous layer washed with diethyl ether (2×100 ml). The combined organics were dried (MgSO4), filtered and the solvent removed in vacuo to leave 2-cyclopentylquinoline (9.98 g, 50.4 mmol) as an oil.

1. customthe ice bath removed
2. stirringthe mixture stirred for a further 10 minutes
3. additiona saturated ammonium chloride solution (40 ml) added slowly
4. customThe resulting reaction mixture
5. additionwas poured into a separating funnel
6. customThe organics were separated
7. washthe aqueous layer washed with diethyl ether (2×100 ml)
8. dry with materialThe combined organics were dried (MgSO4)
9. filtrationfiltered
10. customthe solvent removed in vacuo

ORD record

ord-6ef299c453e641a5a40b6ddbf30a612a

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772227B2