2-Chloroquinoline → HCID 12621791, compound

HRID 2416368Notes

Reaction equation

HRID 2416368 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]#[N:13].[H-].[Na+].Cl[C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1>C1(C)C=CC=CC=1.C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)[C:12]#[N:13]

Participants

6

Reactant 3

HCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 2643022-(quinolin-2-yl)acetonitrile

Product 1

HCID 12621791HCID 12621791, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-quinolylacetonitrile (14.5 g, 86.2 mmol) in toluene (200 mL) was added slowly NaH (6.9 g of 60% oil dispersion, 172 mmol). The reaction mixture was stirred at ambient temperature for 15 min at which point H2 evolution was no longer evident. A solution of 2-chloroquinoline (14.1 g, 86.2 mmol) in toluene (150 mL) was added to the reaction flask, and the reaction mixture was then heated at reflux for 18 h. The reaction mixture was cooled to ambient temperature, diluted with THF, and quenched with H2O. The organic solution was washed with 1N HCl (200 mL), saturated aqueous solution of NaHCO3, and brine. An orange solid precipitated from the organic layer and was isolated via vacuum filtration. The mother liquor was dried over MgSO4 and the volatile components were removed with a rotary evaporator. The resulting solid was combined with the orange powder isolated via filtration. The solid was washed with a mixture of ether and heptane to afford 14.7 g (57.6%) of product. Results of 1H NMR spectroscopy and electrospray mass spectroscopy are consistent with the product. 1H NMR (300 MHz, CDCl3): δ 7.36 (m, 2H), 7.57 (d, J=9.1 Hz, 2H), 7.64 (m, 4H), 7.73 (d, J=8.8 Hz, 2H), 7.86 (d, J=9.1 Hz, 2H).

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. customquenched with H2O
  5. washThe organic solution was washed with 1N HCl (200 mL), saturated aqueous solution of NaHCO3, and brine
  6. customAn orange solid precipitated from the organic layer
  7. customwas isolated via vacuum filtration
  8. dry with materialThe mother liquor was dried over MgSO4
  9. customthe volatile components were removed with a rotary evaporator
  10. customisolated via filtration
  11. washThe solid was washed with a mixture of ether and heptane

Sources & evidence

ORD record
ord-9f8c7362901a4f9eb0f4b216d4441464
Source dataset
uspto-grants-2004_11
Patent number
US06824893B2

Reaction notes

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