HCID 66596834, compound → HCID 66596974, compound

HRID 1811383Notes

Reaction equation

HRID 1811383 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:7]2[C:12]=1[N:11]([CH3:13])[C:10](=[O:14])[CH:9]=[CH:8]2>[C].[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:15][CH:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:7]2[C:12]=1[N:11]([CH3:13])[C:10](=[O:14])[CH:9]=[CH:8]2

Participants

4

Reactant 1

HCID 66596834HCID 66596834, compound

Product 1

HCID 66596974HCID 66596974, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Diethyl 2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethylene)malonate (16.62 g) and 10% palladium carbon (1.6 g) were added to 300 ml of ethanol, followed by catalytic hydrogenation at room temperature and atmospheric pressure for 6 hours. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) to thereby obtain 13.59 g (yield: 81%) of diethyl 2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethyl)malonate as a light yellow oil.

Workup

  1. customfollowed by catalytic hydrogenation at room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-ebba9bf0bbf0412f80f0f07908385e5d
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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