Potassium Carbonate → 2-(3-Vinylphenylamino)-3-nitropyridine

HRID 1953405Notes

Reaction equation

HRID 1953405 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])=[CH2:2].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:1]([C:3]1[CH:4]=[C:5]([NH:6][C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 42600413-Aminostyrene

Product 1

HCID 232981282-(3-Vinylphenylamino)-3-nitropyridineYield 79.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-vinylaniline (8 g), 2-chloro-3-nitropyridine (10.7 g) and potassium carbonate (18.6 g) in dioxane (80 ml) was stirred under reflux for 5 days. The reaction was extracted with chloroform, washed with water, dried over magnesium sulfate and evaporated. After evaporation of the solvent, crude residue was crystallized from methanol to give 2-(3-vinylphenylamino)-3-nitropyridine as an orange crystals (12.9 g).

Workup

  1. temperatureunder reflux for 5 days
  2. extractionThe reaction was extracted with chloroform
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customAfter evaporation of the solvent, crude residue
  7. customwas crystallized from methanol

Sources & evidence

ORD record
ord-d16f2b570ac24227b348df00655d1766
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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