HCID 25242179, compound → 3-fluoro-6-methoxyquinoline

HRID 1852266Notes

Reaction equation

HRID 1852266 reaction equation
Cl[C:2]1[C:11]([F:12])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1>N.[Ni].CO>[F:12][C:11]1[CH:2]=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:14][CH3:15])=[CH:6][CH:5]=2

Participants

5

Reactant 1

HCID 25242179HCID 25242179, compound

Product 1

HCID 113098403-fluoro-6-methoxyquinolineYield 41.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent2×

Procedure

To a suspension of 2,4-dichloro-3-fluoro-6-methoxyquinoline (0.9 g, 3.66 mmol) in ammonia in methanol (10 mL, 462 mmol) was added carefully the slurry of Raney Nickel (5 g, 3.66 mmol) in Methanol (10 mL). The resulting reaction mixture was hydrogenated at 150 psi pressure, stirred at room temperature for 24 h. Filtered the catalyst, washed with methanol, evaporated the filtrate under reduced pressure to afford crude mass, purified by silica gel chromatography eluting with 10%-50% ethyl acetate in pet-ether to afford 3-Fluoro-6-methoxy quinoline (0.27 g, 41%) as pink solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.65 (d, J=2.9 Hz, 1H), 8.01-7.98 (d, J=9 Hz, 1H) 7.67-7.64 (dd, J=9 Hz, J=2.9 Hz 1H), 7.33-7.30 (dd, J=9.0 Hz, J=2.9 Hz, 1H), 7.03 (d, J=2.9 Hz 1H), 3.93 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationFiltered the catalyst
  3. washwashed with methanol
  4. customevaporated the filtrate under reduced pressure
  5. customto afford crude mass
  6. custompurified by silica gel chromatography
  7. washeluting with 10%-50% ethyl acetate in pet-ether

Sources & evidence

ORD record
ord-76799eb4fdf14d26af2ef8f9edcfbe06
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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