Isonicotinic Acid → HCID 22923333, compound

HRID 2257525Notes

Reaction equation

HRID 2257525 reaction equation
S(Cl)(Cl)=O.[C:5]([OH:13])(=O)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCCl.O>[F:14][C:15]1[CH:16]=[C:17]([F:21])[CH:18]=[CH:19][C:20]=1[C:5]([C:6]1[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=1)=[O:13]

Participants

7

Reactant 4

HCID 5922Isonicotinic AcidHCID 97411,3-DifluorobenzeneHCID 24386Thionyl Chloride2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 22923333HCID 22923333, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

219 ml (3.00 mole) of thionyl chloride were added to a solution of 246.2 g (2.00 mole) of isonicotinic acid in 500 ml of 1,2-dichloroethane and the mixture was refluxed for 4 hours. The excess thionyl chloride and the solvent were removed by evaporation at reduced pressure and 392 ml (4.00 mole) of 1,3-difluorobenzene and then, portionwise, 533 g (4.00 mole) of aluminium trichloride were added over the solid residue. Once the exothermal reaction has ended, the mixture was refluxed for 5 hours. it was cooled and poured over a mixture of 3 kg of ice and 1 kg of water, was stirred for 0.5 hours and the phases were separated. The aqueous phase was washed with 1L of methylene chloride, was than basified with 2L of 40% NaOH and extracted with Ch2Cl2 (2 x 1L). The combined organic extracts were dried (MgSO4) and evaporated at reduced pressure to give 179.4 g (41% yield) of the title compound in the form of an ochre coloured oil.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customOnce the exothermal reaction
  3. temperaturethe mixture was refluxed for 5 hours
  4. temperatureit was cooled
  5. customthe phases were separated
  6. washThe aqueous phase was washed with 1L of methylene chloride
  7. extractionextracted with Ch2Cl2 (2 x 1L)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-cdf980efde02428984033892438d6fea
Source dataset
uspto-grants-1997_08
Patent number
US05658916

Reaction notes

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