Hydroxyamine hydrochloride → 4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

HRID 910362Notes

Reaction equation

HRID 910362 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[O:8])=[C:5]([CH3:17])[CH:4]=1)=O.Cl.[OH:19][NH2:20].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:19][N:20]=[CH:1][C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[O:8])=[C:5]([CH3:17])[CH:4]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866114664-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

Product 1

HCID 860706344-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amideYield 58.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a solution of 0.8 g of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 10 ml of ethanol and 5 ml of water, 0.3 g of hydroxyamine hydrochloride and 0.4 g of anhydrous sodium acetate were added with stirring at room temperature, and stirred at the same temperature for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, and precipitated crystal was filtered off, washed with water and dried to obtain 0.5 g of the aimed product as white crystal.

Workup

  1. stirringstirred at the same temperature for 30 minutes
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. customprecipitated crystal
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-0619fc58a6224cea833a067c072b236c
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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