Methanol → Quinoline

HRID 2079935Notes

Reaction equation

HRID 2079935 reaction equation
O1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6](#[N:8])[CH3:7].[CH3:9]O.C(O[CH2:15][CH3:16])(=O)C>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O.C(O)C>[N:8]1[C:6]2[C:5](=[CH:9][CH:15]=[CH:16][CH:7]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 8857Ethyl Acetate2×

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 3

HCID 17887766Palladium barium sulphateCatalystHCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

The present step is a step wherein a triple bond in compound (4-4) is reduced into a double bond to obtain compound (4-5). Compound (4-5) can be obtained using a catalyst such as, for instance, Lindlar catalyst, palladium-barium sulfate or the like, in a solvent such as, for instance, tetrahydrofuran, ethyl acetate, acetonitrile, methanol, ethanol or the like, under hydrogen atmosphere. The preferable solvent is ethyl acetate. To obtain satisfactory results, 0.1 equivalents to 1 equivalents of quinoline may be added based on compound (4-4). The catalyst is used in catalytic amount to excess amount based on compound (4-4). The reaction temperature is room temperature, the reaction time is from 15 minutes to 24 hours, and reaction pressure is from 1 atm to 4 atm.

Sources & evidence

ORD record
ord-1083ddcb762e4c7dbaeb8a50f7719e74
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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