7-Methylisatin → 3-(Benzyloxyimino)-7-methylindolin-2-one

HRID 378705Notes

Reaction equation

HRID 378705 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=O.Cl.[CH2:14]([O:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:14]([O:21][N:22]=[C:7]1[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=2)[NH:9][C:8]1=[O:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 143137-MethylisatinHCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 1361447423-(Benzyloxyimino)-7-methylindolin-2-oneYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4.91 g of 7-methylisatin in 100 ml of ethanol was added a solution of 5.59 g of O-benzylhydroxylamine hydrochloride and 3.29 g of sodium acetate in 40 ml of water at room temperature. The mixture was stirred at room temperature for 3 hours and concentrated. The concentrate was diluted with chloroform and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated. Recrystallization of the crude product from benzene yielded 5.40 g (68%) of the title compound.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with chloroform
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customRecrystallization of the crude product from benzene

Sources & evidence

ORD record
ord-c88441acf57d43f08a95f1b957719fe0
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

Loading…