Ethyl 3-(2-chloro-5,6-dimethyl-3-pyridyl)acrylate → Ethyl 3-(5,6-dimethyl-3-pyridyl)propionate

HRID 224868Notes

Reaction equation

HRID 224868 reaction equation
Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:5]([CH3:15])=[C:4]([CH3:16])[N:3]=1>C(O)C.[Pd]>[CH3:15][C:5]1[CH:6]=[C:7]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=[N:3][C:4]=1[CH3:16]

Participants

4

Reactant 1

HCID 53884840Ethyl 3-(2-chloro-5,6-dimethyl-3-pyridyl)acrylate

Product 1

HCID 14576944Ethyl 3-(5,6-dimethyl-3-pyridyl)propionateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-(2-chloro-5,6-dimethyl-3-pyridyl)acrylate (32.7 gZ) in ethanol (500 ml) was hydrogenated at 25°-30° and 344 kPa using palladium-on-charcoal catalyst (5%, 3 g). The mixture was filtered and the filtrate was evaporated to an oil which was partitioned between chloroform and 2 N hydrochloric acid. The aqueous phase was made basic with aqueous sodium hyroxide, extracted with chloroform and the chloroform extracts were evaporated to give ethyl 3-(5,6-dimethyl-3-pyridyl)propionate (21.8 g, 80%) as an oil.

Workup

  1. customwas hydrogenated at 25°-30°
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to an oil which
  4. customwas partitioned between chloroform and 2 N hydrochloric acid
  5. extractionextracted with chloroform
  6. customthe chloroform extracts were evaporated

Sources & evidence

ORD record
ord-031b94fa27f84dce9de294f6ee626aaf
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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