Tetrahydrofuran → 4-[(2-Butyl-4-quinolinyl)-methyl]-benzonitrile

HRID 2260819Notes

Reaction equation

HRID 2260819 reaction equation
[CH2:1]([C:5]1[CH:14]=[C:13](Cl)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].O1[CH2:20][CH2:19][CH2:18][CH2:17]1>[Zn].BrCC1C=CC(C#N)=CC=1>[CH2:1]([C:5]1[CH:14]=[C:13]([CH2:17][C:18]2[CH:3]=[CH:2][C:1]([C:5]#[N:6])=[CH:20][CH:19]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 110422352-Butyl-4-chloroquinoline

Product 1

HCID 189990714-[(2-Butyl-4-quinolinyl)-methyl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 69459885HCID 69459885, compoundCatalyst

Procedure

Using the procedure of Step G of Example 1, 0.614 g of 4-chloro-2-butyl quinoline of Step D, 0.8 ml of tetrahydrofuran, 0.323 g of tetrakis triphenylphosphine palladium and 10 ml of a 0.5M 4-bromomethyl benzonitrile zinc solution in tetrahydrofuran were reacted to obtain after chromatography on silica (eluant: hexane--ethyl acetate (8-2)) 0.781 g of the desired product.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1a8bb00862a641b186db022687a0e335
Source dataset
uspto-grants-1995_12
Patent number
US05478938

Reaction notes

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