Hydrazine hydrate (1:1) → O-[[4-(trifluoromethyl)phenyl]methyl]hydroxylamine

HRID 1054220Notes

Reaction equation

HRID 1054220 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][CH:4]=1.O.NN>C(O)C>[F:1][C:2]([F:22])([F:23])[C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][NH2:9])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1486319HCID 1486319, compound

Product 1

HCID 2737778O-[[4-(trifluoromethyl)phenyl]methyl]hydroxylamineYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 2-((4-(trifluoromethyl)benzyl)oxy)isoindoline-1,3-dione (9 g, 28.0 mmol) in ethanol (90 mL) was added hydrazine hydrate (1.543 g, 30.8 mmol) at RT. Reaction mixture was stirred for 16 h. Reaction mixture was filtered and filtrate was diluted with water and extracted with EtOAC. The organic layer was separated and distilled out to get the titled compound in 68% yield.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. filtrationwas filtered
  4. additionfiltrate was diluted with water
  5. extractionextracted with EtOAC
  6. customThe organic layer was separated
  7. distillationdistilled out

Sources & evidence

ORD record
ord-e11eaf6e9ffe43d7b39b5fee92b1a6eb
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

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