Ammonium Hydroxide → 5-Methoxypyridin-3-ylamine

HRID 252210Notes

Reaction equation

HRID 252210 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[NH4+:10].[OH-]>O.[O-]S([O-])(=O)=O.[Cu+2].O>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([NH2:10])[CH:3]=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 8171633-Bromo-5-methoxypyridine

Product 1

HCID 127035955-Methoxypyridin-3-ylamine

Reagents, catalysts & solvents 2

HCID 61499Cupric sulfate monohydrateCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 3-bromo-5-methoxypyridine (5.2 g, 27.5 mmol) and CuSO4.H2O (1.37 g, 5.5 mmol) in NH4OH (5 mL) was placed in a sealed tube and heated at 120° C. for 10 hours. The reaction mixture was then cooled to room temperature, diluted with H2O (40 mL), and extracted with EtOAc (3×30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound that was used in the next step with no further purification.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e31b3fe920094371837351538f9ad015
Source dataset
uspto-grants-2011_01
Patent number
US07868026B2

Reaction notes

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