Stannous Chloride → 5-Fluoro-3-(trifluoromethyl)benzene-1,2-diamine

HRID 54366Notes

Reaction equation

HRID 54366 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([F: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]([F:11])=[CH:4][C:3]=1[C:12]([F:15])([F:13])[F:14]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 2230974-Fluoro-2-nitro-6-(trifluoromethyl)aniline

Product 1

HCID 27744615-Fluoro-3-(trifluoromethyl)benzene-1,2-diamineYield 30.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred mixture of 2-amino-5-fluoro-3-nitrobenzotrifluoride (554 mg, 2.47 mmol) in ethanol (10 mL) was added SnCl2 ·2 H2O (2.78 g, 12.36 mmol) in one portion. The mixture was refluxed at 80° C. (oil bath 90° C.) for 1 h, 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 over Mg2SO4 and evaporated to give 148 mg (30%) of 2,3-diamino-5-fluorobenzotrifluoride as a brown solid. 1H NMR (CDCl3): δ3.666 (s, 2H); 3.676 (s, 2H); 6.610 (dd, 1H, J1 =2.4 Hz, J2 =9.0 Hz), 6.703 (dd, 1H, J1 =2.4 Hz, J2 =9.0 Hz).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over Mg2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-677a1fa8a77d4c2c88975a6d77200abc
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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