Water → 4-[(3-Butyl-4-cinnolinyl)-methyl]-benzonitrile
Reaction equation
[CH2:1]([C:5]1[N: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].O.[OH-].[NH4+:18].O1[CH2:23][CH2:22][CH2:21][CH2:20]1>[Cl-].C1(C(C2C=CC=CC=2)(P)CC)C=CC=CC=1.[Ni+2].[Cl-].[Zn].BrCC1C=CC(C#N)=CC=1>[CH2:1]([C:5]1[N:6]=[N:7][C:8]2[C:13]([C:14]=1[CH2:20][C:21]1[CH:5]=[CH:1][C:2]([C:3]#[N:18])=[CH:23][CH:22]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
100 mg of nickel diphenyl phosphino propane chloride were added to a solution of 0.87 g of 3-butyl-4-chloro cinnoline of Step C and 30 ml of tetrahydrofuran and the mixture was refluxed. 10 ml of a 0.5 M solution in tetrahydrofuran of 4-bromomethyl benzonitrile zinc (prepared as Knochel, J. Org. Chem., (1988), Vol. 53. p. 5789 to 5791) were added, followed by stirring for one hour at 50° C., then pouring into ice-cooled water. The solution was alkalized by the addition of ammonium hydroxide, concentrated and extracted with ethyl acetate. The extracts were washed with water, dried and evaporated to dryness. The residue was chromatographed on silica (eluant: ethyl acetate - hexane (1-1)) to obtain 680 mg of the desired product.
Workup
- temperaturethe mixture was refluxed
- additionpouring into ice-
- concentrationconcentrated
- extractionextracted with ethyl acetate
- washThe extracts were washed with water
- customdried
- customevaporated to dryness
- customThe residue was chromatographed on silica (eluant: ethyl acetate - hexane (1-1))
Sources & evidence
- ORD record
- ord-73f3954ac35c44d2b1f2aa02d606a599
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05324839
Reaction notes
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