Hydrazine hydrate (1:1) → (E)-(2-chloro-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)phenyl)methanamine
Reaction equation
[Cl:1][C:2]1[CH:19]=[C:18](/[CH:20]=[CH:21]/[CH:22]([C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=2)[C:23]([F:26])([F:25])[F:24])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>CCO>[Cl:1][C:2]1[CH:19]=[C:18](/[CH:20]=[CH:21]/[CH:22]([C:27]2[CH:28]=[C:29]([Cl:34])[CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:23]([F:25])([F:26])[F:24])[CH:17]=[CH:16][C:3]=1[CH2:4][NH2:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of (E)-2-(2-chloro-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)benzyl)isoindoline-1,3-dione (CI.4 g, 0.76 mmol) in EtOH was added hydrazine hydrate (0.38 g, 7.6 mmol), and the resultant reaction mixture was heated at 80° C. for 2 h. The reaction mixture was filtered, and the filtrate was concentrated. The residue was dissolved in CH2Cl2, washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a gummy liquid (0.3 g), which was carried on to the next step without further purification.
Workup
- customthe resultant reaction mixture
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated
- dissolutionThe residue was dissolved in CH2Cl2
- washwashed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4a392b15337c4f65bceebfe9a5902f8c
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09211281B2
Reaction notes
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