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

HRID 1369065

Reaction equation

HRID 1369065 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-5e82e8807705432a82e25f6eae4d99e0
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Linked notes

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