4-Chlorobenzaldehyde → HCID 13392574, compound

HRID 2413356Notes

Reaction equation

HRID 2413356 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.Cl[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 13392574HCID 13392574, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 25 g of 2-methyl-5-pyridinol, 32 g of 4-chlorobenzaldehyde, 75 g of potassium carbonate and 200 ml of dimethylformamide was heated under refluxing for 6 hours with stirring. After cooling, the mixture was filtered and the filtrate was concentrated. The resulting oily substance was dissolved in diethyl ether, and the solution was washed successively with an aqueous solution of sodium hydroxide and water, and dried over magnesium sulfate. The solvent was then distilled off and the resulting oily substance was dissolved in isopropyl alcohol. To the solution was added concentrated hydrochloric acid, and the resulting hydrochloride was filtered and recrystallized from a mixture of methanol and ethyl acetate to obtain colorless needles. The crystals were added to an aqueous solution of sodium carbonate and the mixture was extracted with dichloromethane. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off to obtain an oily substance which crystallized upon standing. The crystals were recrystallized from hexane to obtain 17 g (35% yield) of 4-(2-methyl-5-pyridyloxy)benzaldehyde as colorless prisms having a melting point of 45°-46° C. and a boiling point of 133° C./2 mmHg (bath temperature).

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 6 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe resulting oily substance was dissolved in diethyl ether
  7. washthe solution was washed successively with an aqueous solution of sodium hydroxide and water
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was then distilled off
  10. dissolutionthe resulting oily substance was dissolved in isopropyl alcohol
  11. additionTo the solution was added concentrated hydrochloric acid
  12. filtrationthe resulting hydrochloride was filtered
  13. customrecrystallized from a mixture of methanol and ethyl acetate
  14. customto obtain colorless needles
  15. extractionthe mixture was extracted with dichloromethane
  16. washThe organic layer was washed with water
  17. dry with materialdried over magnesium sulfate
  18. distillationThe solvent was distilled off
  19. customto obtain an oily substance which
  20. customcrystallized
  21. customThe crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-888553db0cd34f82be350dc0c3894d83
Source dataset
uspto-grants-1985_01
Patent number
US04496735

Reaction notes

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