HCID 19603510, compound → HCID 17812572, compound

HRID 1604582Notes

Reaction equation

HRID 1604582 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[CH:20]=[CH2:21])C1C=CC=CC=1>C(O)C.O1CCOCC1.[OH-].[Pd+2].[OH-]>[CH2:20]([C:14]1[C:13]2[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=2)[N:17]=[C:16]([CH3:19])[CH:15]=1)[CH3:21]

Participants

5

Reactant 1

HCID 19603510HCID 19603510, compound

Product 1

HCID 17812572HCID 17812572, compoundYield 48.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-benzyloxy-2-methyl-4-vinylquinoline (200 mg) and palladium(II) hydroxide (40 mg) in a mixture of ethanol (1.5 ml) and dioxane (1.5 ml) was stirred for 9 hours at ambient temperature under hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by flash chromatography (Ethyl acetate:n-hexane=1:2, V/V) to give 4-ethyl-8-hydroxy-2-methylquinoline (66 mg) as brown oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography (Ethyl acetate:n-hexane=1:2, V/V)

Sources & evidence

ORD record
ord-e62e00b042844594ae05f0cff9c6c4fc
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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