Water → 6-Chloro-N-(4-fluorophenyl)picolinamide

HRID 1491555Notes

Reaction equation

HRID 1491555 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.O>S(Cl)(Cl)=O.C(OCC)C>[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:8]([C:6]2[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)=[O:10])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 97314-FluoroanilineHCID 208126-Chloropicolinic acid

Product 1

HCID 111185076-Chloro-N-(4-fluorophenyl)picolinamideYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 24386Thionyl ChlorideSolvent

Procedure

6-chloropicolinic acid (51.2 g, 0.325 mol) in thionyl chloride (90 ml) was stirred and heated to reflux for 2 hours. The excess thionyl chloride was evaporated in vacuo and diethylether (250 ml) added to the residual 6-chloropicolinoyl chloride. A solution of 4-fluoroaniline (37.5 g, 0.338 mol) in diethylether (100 ml) was added with stirring, maintaining the temperature below 20° C. After the addition, the reaction mixture was stirred overnight at ambient temperature. Water was added to the reaction mixture and the organic layer separated. After a further washing with water and drying with anhydrous magnesium sulphate, the solvent was removed in vacuo to give the title compound as a pale brown solid (66 g, 82%), mp 98° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customThe excess thionyl chloride was evaporated in vacuo and diethylether (250 ml)
  4. additionadded to the residual 6-chloropicolinoyl chloride
  5. temperaturemaintaining the temperature below 20° C
  6. additionAfter the addition
  7. stirringthe reaction mixture was stirred overnight at ambient temperature
  8. customthe organic layer separated
  9. washAfter a further washing with water
  10. dry with materialdrying with anhydrous magnesium sulphate
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c8b2dcfc0b294dc5a4138bb019db73e2
Source dataset
uspto-grants-1994_12
Patent number
US05371061

Reaction notes

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