Oxalyl chloride → 7-fluoro-1-(2-fluoro-phenyl)-3-methyl-1H-quinolin-4-one

HRID 1887811Notes

Reaction equation

HRID 1887811 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[CH:3]=1.[C:20](Cl)(=O)C(Cl)=O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8](=[O:11])[C:9]([CH3:20])=[CH:10][N:12]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 712084951-[4-Fluoro-2-(2-fluoro-phenylamino)-phenyl]-propan-1-one

Product 1

HCID 712089357-fluoro-1-(2-fluoro-phenyl)-3-methyl-1H-quinolin-4-oneYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 mL round bottom flask, 1-[4-fluoro-2-(2-fluoro-phenylamino)-phenyl]-propan-1-one (3.05 g, 11.7 mmol) was added to DMF (4.3 mL) at 0° C. Oxalyl chloride (8.18 mL, 96.7 mmol) was added slowly and the reaction mixture stirred at 0° C. The mixture was then warmed up to room temperature and stirred for 1.5 hr. The mixture was concentrated to dryness and the crude redissolved in toluene (80 mL). The reaction mixture was heated at 115° C. for 24 hr. The mixture was concentrated to dryness and triturated from methanol to afford 7-fluoro-1-(2-fluoro-phenyl)-3-methyl-1H-quinolin-4-one (1.20 g, 37.8%) as a white solid.

Workup

  1. temperatureThe mixture was then warmed up to room temperature
  2. stirringstirred for 1.5 hr
  3. concentrationThe mixture was concentrated to dryness
  4. dissolutionthe crude redissolved in toluene (80 mL)
  5. temperatureThe reaction mixture was heated at 115° C. for 24 hr
  6. concentrationThe mixture was concentrated to dryness
  7. customtriturated from methanol

Sources & evidence

ORD record
ord-a0bc12d08c404f2e8f9f3c2436828414
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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