Sodium Hydroxide → 5-Bromo-2-ethoxypyridin-3-amine

HRID 241052Notes

Reaction equation

HRID 241052 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.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C>[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

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 24479Stannous ChlorideHCID 582557825-Bromo-2-ethoxy-3-nitropyridine

Product 1

HCID 532116995-Bromo-2-ethoxypyridin-3-amineYield 82.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-2-ethoxy-3-nitropyridine (75.2 mg, 0.304 mmol) in ethyl acetate (3 mL) was added tin(II) chloride (289 mg, 1.52 mmol), and the mixture was heated to reflux for 2 h. After cooling to rt, 50% aqueous sodium hydroxide was added dropwise until a sticky brown solid completely formed. Sodium sulfate was then added, and the mixture was stirred for several minutes. The solids were then removed by filtration. The filtrate was dried over sodium sulfate, filtered, and concentrated in vacuo to provide 5-bromo-2-ethoxypyridin-3-amine (53 mg, 0.25 mmol, 80% yield) as a dark blue film. 1H NMR (400 MHz, CDCl3) δ 7.56 (d, 1H), 6.97 (d, 1H), 4.37 (q, 2H), 3.85 (br s, 2H), 1.40 (dd, 3H); MS (EI) for C7H9BrN2O: 217, 219 (Br isotopes, MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. customcompletely formed
  4. customThe solids were then removed by filtration
  5. dry with materialThe filtrate was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cf648f54bfc423388b98d803ddbf538
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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