Water → 4-[(3-Butyl-4-cinnolinyl)-methyl]-benzonitrile

HRID 1110121노트

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HRID 1110121 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 14923Ammonium HydroxideHCID 19595374HCID 19595374, 화합물

생성물 1

HCID 189990754-[(3-Butyl-4-cinnolinyl)-methyl]-benzonitrile

시약·촉매·용매 2

HCID 69459885HCID 69459885, 화합물촉매HCID 86747958Nickel diphenyl phosphino propane chloride촉매

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온도
50 °C

실험 절차

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.

후처리

  1. temperaturethe mixture was refluxed
  2. additionpouring into ice-
  3. concentrationconcentrated
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue was chromatographed on silica (eluant: ethyl acetate - hexane (1-1))

출처 및 근거

ORD 기록
ord-73f3954ac35c44d2b1f2aa02d606a599
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324839

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