Isatin → HCID 136067498, compound

HRID 366020Notes

Reaction equation

HRID 366020 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.[CH3:13][O:14][NH2:15].O.O.O.C([O-])(=O)C.[Na+]>CO.O>[CH3:13][O:14][N:15]=[C:4]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:2]1=[O:3]

Participants

6

Reactant 3

HCID 7054IsatinHCID 521874O-Methylhydroxylamine hydrochlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 136067498HCID 136067498, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 3.8 l of methanol was dissolved 176 g of isatin while heating, and a solution of 100 g of O-methylhydroxylamine hydrochloride and 136 g of sodium acetate trihydrate in 400 ml of water was added thereto. The resulting mixture was stirred at room temperature for 10 minutes, followed by concentration. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and concentrated to give 192 g (91%) of 3-methoxyiminoindolin-2-one. The resulting crude product was used in the subsequent reaction without being purified.

Workup

  1. temperaturewhile heating
  2. concentrationfollowed by concentration
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d4735fc797e44fa1bd90b208377ceb4a
Source dataset
uspto-grants-2000_10
Patent number
US06127544

Reaction notes

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