Isatin → HCID 136088328, compound

HRID 618542Notes

Reaction equation

HRID 618542 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-a156e834f2844ff5902f4615f7b88efc
Source dataset
uspto-grants-1999_09
Patent number
US05952511

Reaction notes

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