Hydrochloric Acid → 4-[(3-Butyl-4-quinolinyl)-methyl]-benzonitrile

HRID 2260817Notes

Reaction equation

HRID 2260817 reaction equation
[CH2:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1Cl)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4].Cl.O1[CH2:21][CH2:20][CH2:19][CH2:18]1>[Zn].BrCC1C=CC(C#N)=CC=1>[CH2:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[CH2:18][C:19]1[CH:2]=[CH:1][C:5]([C:6]#[N:7])=[CH:21][CH:20]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 195953523-Butyl-4-chloro quinoline

Product 1

HCID 189990804-[(3-Butyl-4-quinolinyl)-methyl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 69459885HCID 69459885, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

14 ml of a 0.38M solution of 4-bromomethyl benzonitrile zinc in tetrahydrofuran (prepared by Knochel, J. Org. Chem., (1988) Vol. 53, pages 5789 to 5791) were added to a stirred mixture of 0.720 g of 4-chloro-3-butyl quinoline of Step F with 0.8 ml of tetrahydrofuran and 0.663 g of tetrakis triphenylphosphine palladium. The mixture was stirred for 4 hours at 60° C., then for 16 hours at ambient temperature. The mixture was hydrolyzed with 100 ml of 0.1N hydrochloric acid and then extracted with ethyl acetate. The extracts were washed with a saturated solution of sodium chloride, dried and evaporated to dryness. The residue was chromatographed on silica (eluant: hexane--ethyl acetate (7-3)) to obtain 0.445 g of the desired product.

Workup

  1. waitfor 16 hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with a saturated solution of sodium chloride
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica (eluant: hexane--ethyl acetate (7-3))

Sources & evidence

ORD record
ord-82fa12f025a14e008684eeac7fbb8167
Source dataset
uspto-grants-1995_12
Patent number
US05478938

Reaction notes

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