Hydrazine hydrate (1:1) → O-((4-(trifluoromethyl)phenyl)methyl)hydroxylamine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customReaction mixture
- customReaction mixture
- filtrationwas filtered
- additionfiltrate was diluted with water
- extractionextracted with EtOAC
- customThe organic layer was separated
- distillationdistilled out
Sources & evidence
- ORD record
- ord-e11eaf6e9ffe43d7b39b5fee92b1a6eb
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394300B2
Reaction notes
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