2,3-Difluoroaniline → N-(2,3-difluorophenyl)-3-nitropyridin-4-amine

HRID 253969

Reaction equation

HRID 253969 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:19]>C(O)C.O>[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[NH:19][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 782782,3-DifluoroanilineHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 58180163N-(2,3-difluorophenyl)-3-nitropyridin-4-amineYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-chloro-3-nitropyridine (3.0 g, 18.9 mmol) in dry ethanol as added 2,3-difluorobenzenamine (3.66 g, 28.3 mmol). The reaction mixture was refluxed for 30 min. After cooling and concentration in vacuo to give a brown solid, the crude product was taken up in water and the aqueous solution adjusted to a pH of 8-9 and the solution extracted with EtOAc (3×100 mL). The combined organics were washed with water (3×100 mL) and brine solution (1×100 mL), respectively, dried over Na2SO4, and evaporated in vacuo to give a light brown solid. The crude product was triturated with petroleum ether (3×30 mL) to afford N-(2,3-difluorophenyl)-3-nitropyridin-4-amine (3.7 g, 79% yield) as light yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. temperatureAfter cooling
  3. concentrationconcentration in vacuo
  4. customto give a brown solid
  5. extractionthe solution extracted with EtOAc (3×100 mL)
  6. washThe combined organics were washed with water (3×100 mL) and brine solution (1×100 mL)
  7. dry with materialrespectively, dried over Na2SO4
  8. customevaporated in vacuo
  9. customto give a light brown solid
  10. customThe crude product was triturated with petroleum ether (3×30 mL)

Sources & evidence

ORD record
ord-e9358eacbac64b1db36466971a01d6c1
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Linked notes

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