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

HRID 1110121ノート

反応式

HRID 1110121 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 14923Ammonium HydroxideHCID 19595374HCID 19595374、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 69459885HCID 69459885、化合物触媒HCID 86747958Nickel diphenyl phosphino propane chloride触媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-73f3954ac35c44d2b1f2aa02d606a599
出典データセット
uspto-grants-1994_06
特許番号
US05324839

反応ノート

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