Thionyl Chloride → HCID 23089870, compound

HRID 1863993Notes

Reaction equation

HRID 1863993 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O>O1CCCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 230898882-Chloro-4-(4-chlorophenyl)pyridine-3-carboxylic acid

Product 1

HCID 23089870HCID 23089870, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-4-(4-chlorophenyl)nicotinic acid (2.4 g) in tetrahydrofuran (60 ml) was added thionyl chloride (3.2 g), and the mixture was heated under reflux for 3 hrs. The solvent was evaporated under reduced pressure, and the residue was dissolved in tetrahydrofuran (60 ml). Sodium borohydride (1.5 g) was added by small portions at 0° C., and the mixture was allowed to warm gradually and stirred at room temperature for 2 hrs. Water was added to quench the reaction and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.9 g) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in tetrahydrofuran (60 ml)
  5. additionSodium borohydride (1.5 g) was added by small portions at 0° C.
  6. temperatureto warm gradually
  7. additionWater was added
  8. customto quench
  9. customthe reaction
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed successively with water and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-07a61fb8c9714ec997527bbb5ed85889
Source dataset
uspto-grants-2009_12
Patent number
US07625887B2

Reaction notes

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