HCID 53695966, compound → HCID 18918255, compound

HRID 864864Notes

Reaction equation

HRID 864864 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9](=[CH2:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)C.[Pd]>[CH3:16][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 1

HCID 53695966HCID 53695966, compound

Product 1

HCID 18918255HCID 18918255, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of step (iii) (3.6 g) in absolute ethanol (100 ml) was added 5% palladium/charcoal catalyst, and the mixture hydrogenated at ambient temperature and pressure until the theoretical volume of hydrogen had been consumed. The catalyst was removed by filtration through celite and the filtrate evaporated to yield ethyl 2-(4-dimethylamino-3-pyridyl)propanoate as a pale yellow oil (3.1 g) NMR (d6DMSO): δ1.15 (3H,t); 2.65 (2H,t); 2.8 (6H,s); 2.9 (2H,t); 4.05 (2H,q); 6.8 (2H,d); 8.2 (2H,d); m/e 223 (M+H)+.

Workup

  1. customthe mixture hydrogenated at ambient temperature and pressure until the theoretical volume of hydrogen had been consumed
  2. customThe catalyst was removed by filtration through celite
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-0c062576b90644d099a4719ead92afd6
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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