Hydroxyamine hydrochloride → HCID 86070633, compound

HRID 910359Notes

Reaction equation

HRID 910359 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])=[CH:5][CH:4]=1)=O.Cl.[OH:18][NH2:19].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:18][N:19]=[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])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86611465HCID 86611465, compound

Product 1

HCID 86070633HCID 86070633, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In a solution of 4.11 g of 4-formyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 30 ml of ethanol and 10 ml of water, 1.99 g of hydroxyamine hydrochloride and 2.51 g of anhydrous sodium acetate were added, stirred at room temperature for 3.5 hours. After the completion of the reaction, the reaction mixture was poured in 100 ml of water, and then extracted with ethyl acetate (30 ml×3), the organic phase was washed with 50 ml of saturated sodium hydrogen carbonate aqueous solution, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 3.92 g of the aimed product as white crystal.

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate (30 ml×3)
  3. washthe organic phase was washed with 50 ml of saturated sodium hydrogen carbonate aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washThe residual solid was washed with hexane

Sources & evidence

ORD record
ord-f7ebe17d38004ae2ab25eea93778eb2c
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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