1-Benzylisatin → 1-benzyl-3-hydroxyiminoindol-2-one

HRID 618536Notes

Reaction equation

HRID 618536 reaction equation
[CH2:1]([N:8]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](=O)[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]([N:8]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](=[N:20][OH:21])[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 2647341-BenzylisatinHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 1785168151-benzyl-3-hydroxyiminoindol-2-oneYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 7.11 g of N-benzylisatin in 75 ml of ethanol was added a solution of 3.84 g of hydroxylamine hydrochloride and 3.84 g of sodium acetate in 500 ml of water. The mixture was stirred at room temperature for 1 hour, followed by concentration. The residue was washed with water and recrystallized from ethanol to give 6.11 g (81%) of the title compound as yellow crystals.

Workup

  1. concentrationfollowed by concentration
  2. washThe residue was washed with water
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-92c798a1927c441c814a7f1ebbaeb6ff
Source dataset
uspto-grants-1999_09
Patent number
US05952511

Reaction notes

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