Ethanol → HCID 20257391, compound

HRID 1583940Notes

Reaction equation

HRID 1583940 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]1([CH3:21])[CH3:20])[CH:2]=[CH2:3].C(O)C>[H][H].[Pd]>[CH3:21][C:5]1([CH3:20])[CH2:6][CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[C:10]([CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[CH:9]=2)[N:4]1[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 702EthanolHCID 20257373HCID 20257373, compound2×

Product 1

HCID 20257391HCID 20257391, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

3.7 g of methyl 2-(1-allyl-1,2-dihydro-2,2-dimethylquinolin-6-yl)propionate (Compound 20) was added to ethanol. Palladium-on-carbon was further added to the solution, and the mixture were reacted with stirring at room temperature for 20 hours under atmospheric pressure in hydrogen atmosphere. After the catalyst was filtered off, the filtrate was concentrated, and then purified by column chromatography on silica gel (ether:hexane=1:4) to give 3.0 g of methyl 2-(1,2,3,4-tetrahydro-2,2-dimethyl-1-propylquinolin-6-yl)propionate (Compound 14).

Workup

  1. customthe mixture were reacted
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. custompurified by column chromatography on silica gel (ether:hexane=1:4)

Sources & evidence

ORD record
ord-9fa1fbd4de8b477e9332e6ae5d3521aa
Source dataset
uspto-grants-1985_11
Patent number
US04555513

Reaction notes

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