Triethylamine → 3-Fluoro-7-methoxyquinoline

HRID 454133Notes

Reaction equation

HRID 454133 reaction equation
Cl[C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C>[Pd].C(O)C>[F:12][C:11]1[CH:2]=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6]([O:13][CH3:14])[CH:5]=2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 220305912-Chloro-3-fluoro-7-methoxyquinoline

Product 1

HCID 220308563-Fluoro-7-methoxyquinolineYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-3-fluoro-7-methoxyquinoline (310 mg, 1.47 mmol), triethylamine (310 mg, 0.4 ml, 3.07 mmol) and 10% palladium on activated charcoal (50 mg) in dry ethanol (5 ml) was stirred under hydrogen gas at ambient temperature for 24 hours. The mixture was then filtered through celite. The celite was washed with methanol and the solvent was removed by evaporation from the combined filtrates. The crude material was purified by chromatography on silica, eluting with 10% ethyl acetate in isohexane to give 3-fluoro-7-methoxyquinoline (130 mg, 54%).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washThe celite was washed with methanol
  3. customthe solvent was removed by evaporation from the combined filtrates
  4. customThe crude material was purified by chromatography on silica
  5. washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-73022471c3ff43c886d326df070c7eaf
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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