Stannous Chloride → 5-Chloro-3-(trifluoromethyl)benzene-1,2-diamine
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Cl:11])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].Cl[Sn]Cl>C(O)C>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:11])=[CH:4][C:3]=1[C:12]([F:15])([F:13])[F:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a stirred mixture of 2-amino-5-chloro-3-nitrobenzotrifluoride (250 mg, 1.043 mmol) in ethanol (4 mL) was added SnCl2 ·2H2O (1.174 g, 5.217 mmol) in one portion. The mixture was refluxed at 80° C. (oil bath 90° C.) for 1 h. The solution was cooled to room temperature and ice water (20 g) was added. It was adjusted to pH=7 and extracted with ethyl acetate. The extract was dried (Mg2SO4) and evaporated to give 181 mg (83%) of 2,3-diamino-5-chlorobenzotrifluoride as a brown solid. 1H NMR (CDCl3): δ3.515 (s, 2H); 3.878 (s, 2H); 6.845 (s, 1H); 6.988 (s, 1H).
Workup
- temperatureThe solution was cooled to room temperature
- extractionextracted with ethyl acetate
- dry with materialThe extract was dried (Mg2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-1d513dd08e7d4992ae59343e9d704dab
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05514680
Reaction notes
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