Stannous Chloride → 4,5-Bis(trifluoromethyl)benzene-1,2-diamine

HRID 54398Notes

Reaction equation

HRID 54398 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:14]([O-])=O)[CH:4]=1.Cl[Sn]Cl>C(O)C>[F:1][C:2]([F:17])([F:18])[C:3]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:6]([NH2:7])=[C:5]([NH2:14])[CH:4]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 47376332-Nitro-4,5-bis(trifluoromethyl)aniline

Product 1

HCID 40613654,5-Bis(trifluoromethyl)benzene-1,2-diamineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 122 mg (0.445 mmol) of 4,5-bis(trifluoromethyl)-2-nitroaniline and 498 mg (2.62 mmol) of SnCl2 in 6 mL of ethanol was heated at 70° C. for 2 h. The solution was evaporated to remove the ethanol. The residue was treated with 2N NaOH to pH=13. White precipitate was observed. The mixture was extracted by CHCl3 (3×10 mL). The extract was dried (MgSO4) and evaporated to leave 102 mg (94%) of oil. 1H NMR (CDCl3), 3.70 (mb, 4), 7.069 (s, 2) and some impurity. 19F NMR (CDCl3), 56.659 (s).

Workup

  1. customThe solution was evaporated
  2. customto remove the ethanol
  3. additionThe residue was treated with 2N NaOH to pH=13
  4. extractionThe mixture was extracted by CHCl3 (3×10 mL)
  5. dry with materialThe extract was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c635125421414587ad8e9ff49904da0b
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

Loading…