Stannous Chloride → 2,6 Dichloro-4-fluoro-phenylhydrazine hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH2:10].[N:11]([O-])=O.[Na+].Cl[Sn]Cl>Cl.C(O)(C(F)(F)F)=O.O>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][NH2:11]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. solution of 2,6 Dichloro-4-fluorophenylamine (3.0 g, 16.6 mmol) in 12 M HCl (30 mL) and TFA (20 mL) is added slowly and dropwise NaNO2 (20 mmol, 1.37 mL) in water (6 mL). The reaction is stirred at 0° C. for 1 h. A solution of SnCl2 (5.74 g, 25.6 mmol) in 12 M HCl (16 mL) is added over 15 minutes. The ice bath is removed and the reaction is stirred for 18 h. The reaction is filtered and the solid is washed with isopropyl alcohol. The solid is dried to yield the title compound (3.0 g, 96%). LC-ES/MS m/e 194.0 (M+1)
Workup
- customThe ice bath is removed
- stirringthe reaction is stirred for 18 h
- filtrationThe reaction is filtered
- washthe solid is washed with isopropyl alcohol
- customThe solid is dried
Sources & evidence
- ORD record
- ord-d98ade15bb1a4f60999dc962101ddbd2
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846960B2
Reaction notes
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