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

HRID 1719152Notes

Reaction equation

HRID 1719152 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 g) 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 2N hydrochloric acid. The aqueous phase was made basic with aqueous sodium hydroxide, 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 2N hydrochloric acid
  5. extractionextracted with chloroform
  6. customthe chloroform extracts were evaporated

Sources & evidence

ORD record
ord-9e95fcb8a4d8469e9e3e6d78d76c5428
Source dataset
uspto-grants-1985_09
Patent number
US04539207

Reaction notes

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