Isatin → HCID 136088328, compound

HRID 378706Notes

Reaction equation

HRID 378706 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].Cl.[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:13]([O:20][N:21]=[C:4]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:2]1=[O:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7054IsatinHCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 136088328HCID 136088328, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 5.0 g of isatin in 200 ml of ethanol was added a solution of 9.75 g of O-benzylhydroxylamine hydrochloride and 4.18 g of sodium acetate in 50 ml of water at room temperature. The mixture was stirred at room temperature for 3 hours and concentrated. The concentrate was diluted with ethyl acetate and then washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated. Recrystallization of the crude product from ethanol gave 6.06 g (71%) of 3-(benzyloxyimino)indolin-2-one as yellow crystals.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with ethyl acetate
  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 ethanol

Sources & evidence

ORD record
ord-a6e96843580d4e2797fac3d31a857007
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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