8-Quinolinol, 5-benzyl- → HCID 15631321, compound

HRID 1905388Notes

Reaction equation

HRID 1905388 reaction equation
[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[N:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.C(OCC)(=O)C.[Pt]=O>[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]3[C:9]=2[CH2:10][CH2:11][CH2:12][NH:13]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 814038-Quinolinol, 5-benzyl-

Product 1

HCID 15631321HCID 15631321, compoundYield 102.6%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 702.8 mg (2.99 mmol) of 5-(phenylmethyl)-8-quinolinol in 40 ml of methanol and 8 ml of ethyl acetate under nitrogen was added 200 mg of platinum oxide and the mixture was hydrogenated at 40 PSI for four hours. Filtration through a 0.4 μm polyester membrane filter followed by evaporation yielded 733.8 mg of a dark tan solid. Recrystallization from dichloromethane:hexane and then flash chromatography on 50 g of silica eluted with 3:7 ethyl acetate:petroleum ether provided 534.5 mg: melting point 135°-136° C.

Workup

  1. filtrationFiltration through a 0.4 μm polyester membrane
  2. filtrationfilter
  3. customfollowed by evaporation

Sources & evidence

ORD record
ord-221445675f264bc3b0f68b422ff5a610
Source dataset
uspto-grants-1989_06
Patent number
US04843082

Reaction notes

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