Stannous Chloride → HCID 117601490, compound

HRID 1773756Notes

Reaction equation

HRID 1773756 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:13]=[C:12]([N+:14]([O-])=O)[C:10]([NH2:11])=[C:9]([I:17])[CH:8]=2)=[C:5]([CH3:18])[O:4][N:3]=1.[Sn](Cl)Cl>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:13]=[C:12]([NH2:14])[C:10]([NH2:11])=[C:9]([I:17])[CH:8]=2)=[C:5]([CH3:18])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 117601618HCID 117601618, compound

Product 1

HCID 117601490HCID 117601490, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-(3,5-dimethylisoxazol-4-yl)-2-iodo-6-nitroaniline (393 g, 1.09 mol, 1.0 eq) in ethanol (4 L) was added tin (II) chloride (1.03 kg, 5.46 mol, 5.0 eq). The reaction mixture was stirred at 75° C. for 10 h. The solvent was evaporated and the residue was dissolved in EtOAc (5 L), washed with 1 N sodium hydroxide (3×1 L) (the solid precipitated out should be filtered). The organic phase was dried over Na2SO4 and the solvent was removed to give a residue. The residue was purified by flash chromatography on silica (PE/EA=2:1-3:2) to give 253 g of 5-(3,5-dimethylisoxazol-4-yl)-3-iodobenzene-1,2-diamine as a slightly brown solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc (5 L)
  3. washwashed with 1 N sodium hydroxide (3×1 L) (the solid
  4. customprecipitated out
  5. filtrationshould be filtered)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customthe solvent was removed
  8. customto give a residue
  9. customThe residue was purified by flash chromatography on silica (PE/EA=2:1-3:2)

Sources & evidence

ORD record
ord-ec0af7be91934b469c4b5d7da14ad3a6
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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