Stannous chloride dihydrate → [2-Methoxy-5-(trifluoromethyl)phenyl]hydrazine
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([NH2:11])[C:6](=[CH:9][CH:10]=1)[O:7][CH3:8].[N:14]([O-])=O.[Na+].O.O.Cl[Sn]Cl>>[CH3:8][O:7][C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:13])[F:1])=[CH:4][C:5]=1[NH:11][NH2:14]Participants
4
Procedure
The title compound was prepared by the general procedure described above for Preparations 2a-i using 4-trifluromethyl-o-anisidine (V, R1=R2=H, R3=CF3), (22.7 g), NaNO2 (9.02 g), and SnCl2.2H2O (60 g). Workup gave 18.1 g (74%) of (2-methoxy-5-trifluoromethylphenyl)hydrazine which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ7.23 (d, J=2.0 Hz, 1 H), 7.05 (dd, J=8.2, 2.0 Hz, 1 H), 6.81 (d, J=8.3 Hz, 1 H), 3.89 (s, 3 H).
Sources & evidence
- ORD record
- ord-13a7cdd3f8f24e0fa1fd22959d1259c6
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613786B2
Reaction notes
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