Stannous Chloride → 5-Bromo-2-ethoxypyridin-3-amine

HRID 1695755Notes

Reaction equation

HRID 1695755 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1.[Sn](Cl)Cl>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 582557825-Bromo-2-ethoxy-3-nitropyridine

Product 1

HCID 532116995-Bromo-2-ethoxypyridin-3-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-bromo-2-(ethyloxy)-3-nitropyridine (15.5 g) in EtOAc (300 ml) was treated with tin(II) chloride anhydrate (56.6 g) then heated at reflux for 2.5 hr. The reaction was cooled to RT then evaporated to dryness. The residue was treated with 2M NaOH (aq) (500 ml) that was treated with anhydrous magnesium sulfate (˜50 g) then slurried to give a filterable sludge. The filtrate was separated and the organic phase was washed with brine, dried over magnesium sulfate then evaporated to dryness. The residue was purified by column chromatography on silica, eluting with DCM, to give the title compound.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 2.5 hr
  3. customthen evaporated to dryness
  4. additionThe residue was treated with 2M NaOH (aq) (500 ml) that
  5. additionwas treated with anhydrous magnesium sulfate (˜50 g)
  6. customto give a filterable sludge
  7. customThe filtrate was separated
  8. washthe organic phase was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customthen evaporated to dryness
  11. customThe residue was purified by column chromatography on silica
  12. washeluting with DCM

Sources & evidence

ORD record
ord-51588b5c510a4cabb2d99ade0b930170
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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