Methylhydrazine → (4-fluorophenyl)-acetic acid N-methyl-hydrazide
Reaction equation
[CH3:1][NH:2][NH2:3].[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](Cl)=[O:13])=[CH:7][CH:6]=1>C(Cl)Cl>[CH3:1][N:2]([C:12](=[O:13])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=1)[NH2:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a −78° C. stirred solution of methyl hydrazine (11 mL, 208.5 mmol) in CH2Cl2 (100 mL) is added dropwise a solution of commercially available 4-fluorophenyl-acetyl chloride (12 g, 69.5 mmol) in CH2Cl2 (200 mL). The reaction mixture is stirred for 2 hours at −78° C. and is then slowly warmed to room temperature. The reaction mixture is filtered and the filtrate concentrated under reduced pressure to give a pale yellow oil. Purification over silica (EtOAc) affords 7.6 g (61% yield) of the desired product: 1H NMR (300 MHz, CDCl3) δ 7.28-7.23 (m, 2H), 6.99-6.92 (m, 2H), 3.87 (s, 2H), 3.190 (s, 2H), 3.11 (s, 3H); ESI/MS: 183.1 (M+H).
Workup
- temperatureis then slowly warmed to room temperature
- filtrationThe reaction mixture is filtered
- concentrationthe filtrate concentrated under reduced pressure
- customto give a pale yellow oil
- customPurification over silica (EtOAc)
Sources & evidence
- ORD record
- ord-03ce6c4a41134bc8a9af246a863c5c27
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06677337B2
Reaction notes
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