Stannous chloride dihydrate → 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine
Reaction equation
[Cl:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([NH2:8])[CH:7]=1.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O.CCO>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][C:3]=1[C:12]([F:13])([F:14])[F:15]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 5-chloro-2-nitro-4-(trifluoromethyl)phenylamine (2 g, 8.3 mmol, Oakwood) in EtOAc (26 mL) and EtOH (13 mL) was added tin (II) chloride dihydrate (13.1 g, 45 mmol, Aldrich). The reaction mixture was stirred at 70° C. for 1 h. The light-yellow reaction solution was poured to crushed ice (50 mL) and carefully neutralized using saturated aqueous solution of NaHCO3. The resulting suspension was extracted with EtOAc (3×60 mL). The combined organic extracts were dried over MgSO4, filtered and the filtrate evaporatedcon in vacuo to give the title compound as white solid, which was used in the next step without additional purification. MS (ESI, pos. ion) m/z: 211.4 (M+1).
Workup
- additionThe light-yellow reaction solution was poured
- extractionThe resulting suspension was extracted with EtOAc (3×60 mL)
- dry with materialThe combined organic extracts were dried over MgSO4
- filtrationfiltered
Sources & evidence
- ORD record
- ord-08d34082e23a46dc99fd4e18afff31f5
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582761B2
Reaction notes
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