Stannous Chloride → 4-Chloro-3,5-difluorobenzene-1,2-diamine

HRID 1780997Notes

Reaction equation

HRID 1780997 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4]([C:6]([N+:10]([O-])=O)=[CH:7][C:8]=1[F:9])[NH2:5].Cl[Sn]Cl>C(O)C>[Cl:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([NH2:10])=[C:4]([NH2:5])[C:3]=1[F:13]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 106560013-Chloro-2,4-difluoro-6-nitroaniline

Product 1

HCID 107024804-Chloro-3,5-difluorobenzene-1,2-diamineYield 95.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 348 mg (1.67 mmol) of 3-chloro-2,4-difluoro-6-nitroaniline and 1.57 g (8.28 mmol) of SnCl2 in 8 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 with CHCl3 (3×10 mL). The extract was dried (MgSO4) and evaporated to leave a red solid (285 mg, 95%); mp 77°-78° C.; 1H NMR (CDCl3), 3.156 (b, 2), 3.704 (b, 2), 6.352 (dd, 1, J=1.86, 9.95).

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 with CHCl3 (3×10 mL)
  5. dry with materialThe extract was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3cada9c9acb74b5d838041f2015ca3bb
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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