Aniline → 3-nitro-N-phenylpyridin-4-amine

HRID 2177623Notes

Reaction equation

HRID 2177623 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([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[N+:8]([C:7]1[CH:2]=[N:3][CH:4]=[CH:5][C:6]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 6120053-nitro-N-phenylpyridin-4-amineYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-chloro-3-nitropyridine (15.8 g, 100 mmol) and aniline (11.1 g, 120 mmol) in dioxane (150 mL) was added was added K2CO3 (39 g, 120 mmol). The reaction was heated to reflux for 10 h and then purified by silica gel chromatography using petroleum etherethyl acetate to provide the product as a yellow solid (20 g, 93%).

Workup

  1. additionwas added
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 10 h
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-8612844333f5423ba7139796c477b82e
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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