2-Chloropyridine → 72358-70-4

HRID 1623042Notes

Reaction equation

HRID 1623042 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[OH-].[Na+]>C(OCC)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 97314-FluoroanilineHCID 14798Sodium Hydroxide

Product 1

HCID 430704972358-70-4Yield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 29.34 g (0.264 mol) of 4-fluoroaniline (1) and 29.98 g (0.264 mol) of 2-chloropyridine (2) was heated at 150° C. for 2 h. After having been cooled down to RT, it was distributed between 500 ml of 1N NaOH and 500 ml of ethyl acetate. The aqueous phase was extracted twice with in each case 300 ml of ethyl acetate and the combined organic phases were dried with magnesium sulfate. After the solvent had been evaporated, the residue was taken up in 500 ml of ethyl acetate and approx. 40 g of active charcoal were added. The mixture was stirred at RT for 10 minutes and filtered through kieselguhr. The active charcoal was rewashed 4 times with in each case 1 l of ethyl acetate. The solvent was removed in vacuo (i.v.) and the residue was precipitated from 120 ml of ethyl acetate. The solid was filtered off with suction and dried at 50° C. i.v. 41 g of 2-(p-fluoroanilino)pyridine (3) were obtained;

Workup

  1. temperatureAfter having been cooled down to RT
  2. extractionThe aqueous phase was extracted twice with in each case 300 ml of ethyl acetate
  3. dry with materialthe combined organic phases were dried with magnesium sulfate
  4. customAfter the solvent had been evaporated
  5. additionapprox. 40 g of active charcoal were added
  6. filtrationfiltered through kieselguhr
  7. customThe solvent was removed in vacuo (i.v.)
  8. customthe residue was precipitated from 120 ml of ethyl acetate
  9. filtrationThe solid was filtered off with suction
  10. customdried at 50° C. i.v

Sources & evidence

ORD record
ord-0197631cdd324e5fbe1433f3e2efe387
Source dataset
uspto-grants-2014_07
Patent number
US08778955B2

Reaction notes

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