7-Allyl-5-fluoro-8-quinolinol → 5-Fluoro-7-propyl-8-quinolinol

HRID 1095221Notes

Reaction equation

HRID 1095221 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([F:15])[CH:5]=1)[CH:2]=[CH2:3].[H][H]>[Pd].CO>[F:15][C:6]1[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[C:13]([OH:14])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2

Participants

5

Reactant 2

HCID 667838147-Allyl-5-fluoro-8-quinolinolHCID 178418361HCID 178418361, compound

Product 1

HCID 667851165-Fluoro-7-propyl-8-quinolinolYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

After a 100 mL three-neck flask equipped with a magnetic stirrer, a reflux condenser and a thermometer was replaced with Ar, 40.0 mL of methanol, 5 wt % Pd/C (0.40 g) and 7-allyl-5-fluoro-8-quinolinol (4.09 g) were thrown thereto and the mixture was stirred under slight pressurization of hydrogen. After replaced with Ar, the mixture was filtered to remove Pd/C and the filtrate was concentrated to give 3.98 g of 5-fluoro-7-propyl-8-quinolinol as a pale purple solid (yield: 96.0%).

Workup

  1. customAfter a 100 mL three-neck flask equipped with a magnetic stirrer, a reflux condenser
  2. filtrationthe mixture was filtered
  3. customto remove Pd/C
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-533b04befecd4249a27b3c5e0ef33dcc
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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