Ethylamine → N-Ethyl-3-nitropyridin-4-amine

HRID 1817147Notes

Reaction equation

HRID 1817147 reaction equation
Cl.CO[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].[CH2:13]([NH2:15])[CH3:14]>C(O)C.O>[CH2:13]([NH:15][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11])[CH3:14]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 3558314-Methoxy-3-nitropyridine hydrochloride

Product 1

HCID 21937597N-Ethyl-3-nitropyridin-4-amineYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Methoxy-3-nitropyridine hydrochloride (11.2 g, 58.9 mmol) in ethanol (75 ml) was treated with a 70% solution of ethylamine in water (64 ml) and heated under reflux for 2 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue dissolved in ethyl acetate and water. The mixture was extracted (×3) with ethyl acetate, washed with water and saturated aqueous sodium chloride solution before drying over magnesium sulfate. Evaporation of the solvent afforded the title compound (11.7 g, 96%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate
  5. extractionThe mixture was extracted (×3) with ethyl acetate
  6. washwashed with water and saturated aqueous sodium chloride solution
  7. dry with materialbefore drying over magnesium sulfate
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c98222fc8f0f467294076e546512ad1b
Source dataset
uspto-grants-2009_10
Patent number
US07598251B2

Reaction notes

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