4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile → 4-[1,1-Dimethyl-3-(2-quinolyl)-2-propynyloxy]benzonitrile

HRID 892592ノート

反応式

HRID 892592 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]=[C:8]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N+:15]=3[O-])[C:7]=2[CH:25]=1)#[N:2].CC1(C)CC(C2C=CC=CN=2)C2C=C(C(O)=O)C=CC=2O1.CC(C)(OC1C=CC(C#N)=CC=1)C#C>C(NCC)C.[Pd](Cl)Cl.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][C:10]([CH3:13])([O:11][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:25][CH:7]=1)[C:9]#[C:8][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

参加物

8

反応物 3

HCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrileHCID 150389033,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran-6-carboxylic acidHCID 198956762-(6-cyano-2,2-dimethyl-2H-1-benzopyran-4-yl)quinoline 1-oxide

生成物 1

HCID 198956464-[1,1-Dimethyl-3-(2-quinolyl)-2-propynyloxy]benzonitrile

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24290Palladium Chloride触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8021Diethylamine溶媒

実験手順

The 2,2-dimethyl-4-(2-quinolyl)-2H-1-benzopyran-6-carbonitrile used as the starting material was prepared as follows: (A) 5.1 g of 2-iodoquinoline were added at room temperature to a solution of 18 mg of palladium(II) chloride, 52 mg of triphenylphosphine and 38 mg of copper(I) iodide in 100 ml of diethylamine. 3.7 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile were added. After stirring at room temperature for 18 hours the mixture was evaporated and the residue was dissolved in ethyl acetate and water. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:2) for the elution to give 5.8 g of 4-[1,1-dimethyl-3-(2-quinolyl)-2-propynyloxy]benzonitrile as a yellow gum. (B) 5.8 g of 4-[1,1-dimethyl-3-(2-quinolyl)-2-propynyloxy]benzonitrile were heated at reflux for 2 hours in 50 ml of dichlorobenzene. The mixture was allowed to cool to room temperature and was then evaporated to dryness. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) for the elution. The product was recrystallized from isopropanol to give 2.1 g of 2,2-dimethyl-4-(2-quinolyl)-2H-1-benzopyran-6-carbonitrile of melting point 102°-104° C.

後処理

  1. customwas prepared
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

出典と根拠

ORDレコード
ord-01cb704468804f05a73a93b465c38751
出典データセット
uspto-grants-1992_06
特許番号
US05118694

反応ノート

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