Stannous Chloride → 4-Trifluoromethyl-1,2-phenylenediamine

HRID 439538Notes

Reaction equation

HRID 439538 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(O)C>[F:12][C:11]([F:13])([F:14])[C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([NH2:1])[CH:10]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 67865Benzenamine, 2-nitro-4-(trifluoromethyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 5208224-Trifluoromethyl-1,2-phenylenediamineYield 96.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-nitro-4-trifluoromethylaniline (5.000 g, 24.26 mmol, Aldrich, used as received) and SnCl2 ·2 H2O (20.00 g, 88.64 mmol, Aldrich, used as received) in absolute ethanol (50 mL) was refluxed for 45 min. It was then poured into ice (85 g) and basified with 10% aq. NaHCO3 (250 mL). The resulting suspension was extracted with ethyl acetate (400 mL). The ethyl acetate extract was dried over Na2SO4 and evaporated to give 4.14 g (87%) of pure 4-trifluoromethyl-1,2-phenylenediamine as a red powder.

Workup

  1. extractionThe resulting suspension was extracted with ethyl acetate (400 mL)
  2. extractionThe ethyl acetate extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-40cfdadaba12428c9cb4cef4fd0a6ce6
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

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