Ethanol → 2-Amino-6-bromo-3-methoxypyridine

HRID 1962227Notes

Reaction equation

HRID 1962227 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.C(O)C.[Cl-].[NH4+]>[Fe].O>[NH2:8][C:6]1[C:5]([O:11][CH3:12])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 226151626-Bromo-3-methoxy-2-nitropyridine

Product 1

HCID 575629062-Amino-6-bromo-3-methoxypyridine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
72.5 °C

Procedure

To a heterogeneous solution of 6-bromo-3-methoxy-2-nitropyridine (32) (2.32 g, 10 mmol) in of ethanol:water (40 mL, each) were added iron powder (2.8 g, 50 mmol), followed by ammonium chloride (2.64 g, 50 mmol) at room temperature. The resulting heterogeneous mixture was then stirred at 70-75° C. for 15 minutes, filtered through celite (when hot), washed with ethanol (2×50 mL) and solvent was then removed under reduced pressure. The residue upon dilution with water afforded a solid, which was isolated by filtration to give 2-amino-6-bromo-3-methoxypyridine (33). LCMS: purity: 95%, MS (m/z): 203 (MH+).

Workup

  1. filtrationfiltered through celite (when hot)
  2. washwashed with ethanol (2×50 mL) and solvent
  3. customwas then removed under reduced pressure
  4. customThe residue upon dilution with water afforded a solid
  5. customwhich was isolated by filtration

Sources & evidence

ORD record
ord-7519d7d9321847c399e104bb1e896dc9
Source dataset
uspto-grants-2013_04
Patent number
US08415365B2

Reaction notes

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