Potassium Carbonate → 2-[3-(2-Naphthyl)phenylamino]-3-nitropyridine

HRID 2086790Notes

Reaction equation

HRID 2086790 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH:14][C:19]2[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 27601672-(3-Aminophenyl)naphthalene

Product 1

HCID 227244452-[3-(2-Naphthyl)phenylamino]-3-nitropyridineYield 67.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(2-naphthyl)aniline (5.0 g), 2-chloro-3-nitropyridine (3.62 g) and potassium carbonate (6.31 g) in dioxane (50 ml) was stirred under reflux for 6 days. The reaction mixture was extracted with chloroform and evaporated. Crude residue was chromatographed on silica gel to give 2-[3-(2-naphthyl)phenylamino]-3-nitropyridine as an orange crystal (5.23 g).

Workup

  1. temperatureunder reflux for 6 days
  2. extractionThe reaction mixture was extracted with chloroform
  3. customevaporated
  4. customCrude residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0587f41f17724b97b166404a1c09e2d9
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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