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

HRID 53808Notes

Reaction equation

HRID 53808 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

p 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 2 N 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 2 N 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-b0f87a1b3f1f410ca61a6fe6a8fdbc6c
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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