Quinoline → Methyl 5-ethenyl-2-hydroxybenzoate

HRID 1464155Notes

Reaction equation

HRID 1464155 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[CH:2].N1C2C(=CC=CC=2)C=CC=1>C(OCC)C.[Pd]>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[CH2:2]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 14172485Methyl 5-ethynyl-2-hydroxybenzoate

Product 1

HCID 19423384Methyl 5-ethenyl-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

Methyl 5-ethynyl-2-hydroxybenzoate (8 g, 45.4 mmol), prepared according to Example 1b, was dissolved in a mixture of diethyl ether and light petroleum (200+200 ml) in a hydrogenation flask. Quinoline (1.7 ml) and palladium on CaCO3, poisoned with Pb (Lindlar catalyst; 200 mg) were added, and the flask was attached to an atmospheric pressure hydrogenation apparatus. The mixture was stirred for 2 h at room temperature, by then the calculated amount of hydrogen had been consumed. The catalyst was filtered off and the solution was evaporated to dryness. The product was purified by flash column chromatograpy on silica, using toluene as an eluent. A nearly quantitative yield was obtained.

Workup

  1. additionwere added
  2. customby then the calculated amount of hydrogen had been consumed
  3. filtrationThe catalyst was filtered off
  4. customthe solution was evaporated to dryness
  5. customThe product was purified by flash column chromatograpy on silica
  6. customA nearly quantitative yield was obtained

Sources & evidence

ORD record
ord-57b0de93cf334c6eac232f54ebb1ff04
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

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