Water → N-Benzyl-5-hydroxyisatin

HRID 1993495Notes

Reaction equation

HRID 1993495 reaction equation
[CH2:1]([N:8]1[C:18]2[C:13](=[CH:14][C:15]([O:19]C)=[CH:16][CH:17]=2)[C:11](=[O:12])[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].O>ClCCl>[CH2:1]([N:8]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[C:11](=[O:12])[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 11357627N-Benzyl-5-methoxyisatin

Product 1

HCID 59134289N-Benzyl-5-hydroxyisatinYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-benzyl-5-methoxyisatin (3.0 g, 11.2 mmol) in dichloromethane (60 mL), aluminum chloride (3.7 g, 28.1 mmol) was added, and the resulting mixture was stirred at 100° C. for 1 hour. Water was added thereto, and the resulting solution was extracted with ethyl acetate. The resulting organic phase was washed with saturated aqueous sodium hydrogencarbonate solution and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to obtain the aimed product (yield: 78%).

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe resulting organic phase was washed with saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialwith saturated sodium chloride solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3e4b16864b8d4a9b85001c29a84007e1
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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