Ammonia → 6-Fluoro-1-methyl-4(1H)-quinolinone

HRID 622688Notes

Reaction equation

HRID 622688 reaction equation
IC.[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[OH:14].[C:15](=O)([O-])[O-].[K+].[K+].N>O1CCCC1>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:15])[CH:9]=[CH:8][C:7]2=[O:14]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 178516423HCID 178516423, compound

Product 1

HCID 212915056-Fluoro-1-methyl-4(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodomethane (6.9 ml) was added to a stirred suspension of 6-fluoro-4-hydroxyquinoline (16.3 g) and anhydrous potassium carbonate (15.2 g) in dry tetrahydrofuran (100 ml) at ambient temperature and stirring was continued for 18 hours. More iodomethane (1.8 ml) and anhydrous potassium carbonate (3.8 g) were added and stirring was continued for 4 hours at ambient temperature. Concentrated aqueous ammonia (specific gravity 0.88; 100 ml) was added and the mixture was evaporated to dryness. The residue was treated with water (200 ml) and extracted with dichloromethane (2×400 ml). The extract was dried and evaporated to dryness. The residue was crystallised from ethyl acetate to give the novel compound 6-fluoro-1-methyl-4-quinolone, m.p. 88°-89°.

Workup

  1. stirringstirring
  2. waitwas continued for 4 hours at ambient temperature
  3. customthe mixture was evaporated to dryness
  4. additionThe residue was treated with water (200 ml)
  5. extractionextracted with dichloromethane (2×400 ml)
  6. customThe extract was dried
  7. customevaporated to dryness
  8. customThe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-a9fccdfaa3004d5f96a9822d69c0f069
Source dataset
uspto-grants-1988_09
Patent number
US04772614

Reaction notes

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