Hydroxyamine hydrochloride → HCID 178467918, compound

HRID 365993Notes

Reaction equation

HRID 365993 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH2:9]([O:11][CH:12]([O:25][CH2:26][CH3:27])[CH2:13][N:14]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17](=O)[C:15]1=[O:16])[CH3:10]>O.C(O)C>[CH2:9]([O:11][CH:12]([O:25][CH2:26][CH3:27])[CH2:13][N:14]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17](=[N:2][OH:3])[C:15]1=[O:16])[CH3:10]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 22013068HCID 22013068, compound

Product 1

HCID 178467918HCID 178467918, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5.38 g of hydroxylamine hydrochloride and 5.38 g of sodium acetate in 40 ml of water was added to a suspension of 11.1 g of 1-(2,2-diethoxyethyl)isatin in 100 ml of ethanol. The mixture was stirred at room temperature for 1 hour, followed by concentration. The concentrate was diluted with chloroform and washed with an aqueous solution of sodium chloride. The chloroform layer was dried over anhydrous sodium sulfate and concentrated, and the residue was recrystallized from ethyl acetate to obtain 7.10 g (61%) of 1-(2,2-diethoxyethyl)-3-(hydroxyimino)indolin-2-one as yellow crystals.

Workup

  1. concentrationfollowed by concentration
  2. additionThe concentrate was diluted with chloroform
  3. washwashed with an aqueous solution of sodium chloride
  4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9a2493874ce343c99117e412e9e7d681
Source dataset
uspto-grants-2000_10
Patent number
US06127544

Reaction notes

Loading…