HCID 68463193, compound → HCID 68462790, compound

HRID 2250395Notes

Reaction equation

HRID 2250395 reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[N:7]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[N:7]=1

Participants

4

Reactant 1

HCID 68463193HCID 68463193, compound2×

Product 1

HCID 68462790HCID 68462790, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6.2 g (E)-3-(6-acetylamino-4-methyl-pyridin-2-yl)-acrylic acid methyl ester (compound D2) are dissolved in 250 ml of ethyl acetate. Subsequently, 1.86 g palladium on active carbon (10% Pd) are added. The suspension is vigorously stirred at r.t. for 14 h under a hydrogen atmosphere. Then the catalyst is removed by filtration over kieselguhr and rinsed with ethyl acetate. The filtrate is concentrated to dryness to afford 6.16 g of the title compound as a colourless solid. M.p. 82° C. ESI-MS: 237.1 (MH+). TLC: Rf=0.18 (cyclohexane/ethyl acetate 2:1).

Workup

  1. customThen the catalyst is removed by filtration over kieselguhr
  2. washrinsed with ethyl acetate
  3. concentrationThe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-28fcf6d86eb94455973daae3d638e060
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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