Propionic Acid → HCID 13384143, compound

HRID 2287211Notes

Reaction equation

HRID 2287211 reaction equation
[CH2:1]([C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[N:9]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:19](O)(=[O:22])[CH2:20][CH3:21]>C(OC(=O)CC)(=O)CC.[Zn]>[C:2]1([CH2:1][CH:8]([NH:9][C:19](=[O:22])[CH2:20][CH3:21])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1032Propionic AcidHCID 14798Sodium HydroxideHCID 136230336HCID 136230336, compound

Product 1

HCID 13384143HCID 13384143, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 31263Propionic anhydrideSolvent

Procedure

To a solution of 42.4 g (0.2 mol) of benzyl-2-pyridylketoxime (E. Niemers and R. Hiltmann, Synth. 1976, 593), 2 g of sodium hydroxide and 0.2 g of mercuric chloride in 300 ml of propionic acid and 100 ml of propionic acid anhydride, were added 52.4 g (0.8 mol) of zinc powder with stirring in portions of 0.5 g in the course of one hour. The solution became warm and turned purple. Stirring was continued at 80° C. until the purple colour turned to yellow (ca. 3 hours). The reaction mixture was cooled and filtered. The residue was thoroughly washed with water and then with chloroform and the chloroform solution obtained was successively washed with water, aqueous sodium bicarbonate and again with water. The solvent was distilled off and the residue was sublimed. The oily product was crystallised from a mixture of ethanol and petroleum ether (boiling range 60°-80° C.). N-[2-phenyl-1-(2-pyridyl)ethyl]propionamide was obtained as a white solid, melting point 91°-93° C.

Workup

  1. temperatureThe solution became warm
  2. stirringStirring
  3. customwas continued at 80° C. until the purple colour
  4. customturned to yellow (ca. 3 hours)
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. washThe residue was thoroughly washed with water
  8. customwith chloroform and the chloroform solution obtained
  9. washwas successively washed with water, aqueous sodium bicarbonate and again with water
  10. distillationThe solvent was distilled off
  11. customThe oily product was crystallised from a mixture of ethanol and petroleum ether (boiling range 60°-80° C.)

Sources & evidence

ORD record
ord-d6cae5418ea94fc7b7b9a25c8e87c1d2
Source dataset
uspto-grants-1981_05
Patent number
US04269834

Reaction notes

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