p-Toluidine → (RS)-1-Benzyl-3-hydroxy-3-((4-methylphenyl)aminocarbonylmethyl)indolin-2-one

HRID 1953308ノート

反応式

HRID 1953308 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[CH2:20]([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH2:37][C:38](OCC)=[O:39])([OH:36])[C:28]1=[O:43])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1.O>[CH2:20]([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([OH:36])([CH2:37][C:38]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[O:39])[C:28]1=[O:43])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

7

反応物 4

HCID 7813p-ToluidineHCID 8058HexaneHCID 2645481-Benzyl-3-(ethoxycarbonylmethyl)-3-hydroxyindolin-2-oneHCID 178418339Butyllithium

生成物 1

HCID 22013019(RS)-1-Benzyl-3-hydroxy-3-((4-methylphenyl)aminocarbonylmethyl)indolin-2-one収率 45.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 0.254 g of p-toluidine in 10 ml of dry tetrahydrofuran was added dropwise 1.3 ml of a 1.59M hexane solution of n-butyl lithium at -78° C. under a nitrogen atmosphere, followed by stirring at that temperature for 10 minutes. To the mixture was added a solution of 0.299 g of 1-benzyl-3-(ethoxycarbonylmethyl)-3-hydroxyindolin-2-one in 5 ml of dry tetrahydrofuran at -78° C., followed by stirring at that temperature for 30 minutes. Water was added to the reaction mixture, and the product was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give 0.161 g (44%) of the title compound.

後処理

  1. stirringby stirring at that temperature for 30 minutes
  2. extractionthe product was extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-c2b3ca85e9674608aa5cc6c870f4ae4f
出典データセット
uspto-grants-2000_09
特許番号
US06114536

反応ノート

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