Aniline → 3-nitro-N-phenylpyridin-2-amine

HRID 486605Notes

Reaction equation

HRID 486605 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)(=O)C>[NH:11]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 6117993-nitro-N-phenylpyridin-2-amineYield 90.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 11.21 g (70 mmol) of 2-chloro-3-nitropyridine and 19.56 g (210 mmol) of aniline was heated under stirring at 100° C. for 1 h. The reaction liquid was cooled to room temperature and dissolved in ethyl acetate. The solution was washed with an aqueous citric acid solution and then with water. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was recrystallized from ethyl acetate/n-hexane to obtain 13.7 g of the title compound.

Workup

  1. temperaturewas heated
  2. customThe reaction liquid
  3. temperaturewas cooled to room temperature
  4. washThe solution was washed with an aqueous citric acid solution
  5. dry with materialAfter drying over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e3c59e7361ea4b4aa3335668b00bee68
Source dataset
uspto-grants-1994_03
Patent number
US05292758

Reaction notes

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