Hydrochloric Acid → 4,6-Dichloro-3-hydroxy-3-(2-naphthyl)oxindole

HRID 1369065

反応式

HRID 1369065 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C([Li])CCC.[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]2[C:19]=1[C:20](=[O:29])[C:21](=[O:28])[NH:22]2.Cl>C1COCC1.CCCCCC>[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]2[C:19]=1[C:20]([OH:29])([C:2]1[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=1)[C:21](=[O:28])[NH:22]2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 113722-BromonaphthaleneHCID 2519084,6-DichloroisatinHCID 178418339Butyllithium

生成物 1

HCID 185186054,6-Dichloro-3-hydroxy-3-(2-naphthyl)oxindole収率 27%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

To a solution of 2-bromonaphthalene (2.952 g) in anhydrous THF (25 mL) was added portion wise a solution of n-butyl lithium in n-hexane (1.55 N, 10.12 mL) at −78° C. The reaction solution was stirred for 30 minutes. To the mixture was then added portion wise a solution of 4,6-dichloroisatin (1.54 g) in anhydrous THF (25 ml) for 50 minutes. The reaction mixture was stirred for 2 hours. Then the mixture was allowed to warm to room temperature. To the mixture was added 1N HCl and extracted by ethyl acetate. The organic phase was separated, washed with 1N HCl and brine and dried over MgSO4 and concentrated . Purification was carried out by silica gel chromatography (hexane:ethyl acetate, 2:1 to 1:1 gradient) to give the title compound (0.652 g, yield: 27%).

後処理

  1. stirringThe reaction mixture was stirred for 2 hours
  2. extractionextracted by ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with 1N HCl and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification

出典と根拠

ORDレコード
ord-5e82e8807705432a82e25f6eae4d99e0
出典データセット
uspto-grants-2003_06
特許番号
US06576656B1

関連ノート

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