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

HRID 333535Notes

Reaction equation

HRID 333535 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(N(CC)CC)C>C(O)CCC>[N+:8]([C:7]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 6117993-nitro-N-phenylpyridin-2-amineYield 85.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-chloro-3-nitropyridine (25 g, 158 mmol), aniline (17.62 g, 189 mmol), and triethylamine (19.15 g, 189 mmol) were mixed in 1-butanol (500 mL). The reaction was heated to reflux overnight. After it cooled to room temperature, the solvent was distilled. The residue was purified by column chromatography using hexanes/ethyl acetate to give 3-nitro-N-phenylpyridin-2-amine (29 g, 85% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. distillationthe solvent was distilled
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a73a65a7ac94418eaa2c4299ee2effe2
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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