Hydrazine hydrate (1:1) → 4-(Perfluoroethoxy)benzohydrazide
Reaction equation
[F:1][C:2]([F:19])([O:7][C:8]1[CH:18]=[CH:17][C:11]([C:12](OCC)=[O:13])=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].O.[NH2:21][NH2:22]>CCO>[F:1][C:2]([F:19])([O:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([NH:21][NH2:22])=[O:13])=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To a solution of ethyl 4-(perfluoroethoxy)benzoate (4.58 g, 16.1 mmol) in EtOH (16 mL) was added hydrazine monohydrate (1.96 mL, 40.3 mmol) and the reaction was heated at 85° C. for 36 hours. The reaction was cooled and poured into ice water (100 mL). A white gel-solid formed and was filtered through a Büchner funnel under vacuum. The solid was dried in a vacuum oven at 45° C. overnight to provide 4-(perfluoroethoxy)benzohydrazide as an off-white solid (3.177 g, 73%): mp 117-119.5° C.; 1H NMR (400 MHz, CDCl3) δ 7.83-7.76 (m, 2H), 7.36 (s, 1H), 7.31 (d, J=8.8 Hz, 2H), 4.13 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −86.01, −87.83; ESIMS m/z 269 [(M−H]−).
Workup
- temperatureThe reaction was cooled
- customA white gel-solid formed
- filtrationwas filtered through a Büchner funnel under vacuum
- customThe solid was dried in a vacuum oven at 45° C. overnight
Sources & evidence
- ORD record
- ord-b5cdac5d174b47f5b9c7cea9da5e00d2
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440964B2
Reaction notes
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