Benzoic Acid → 6-Fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate

HRID 358679Notes

Reaction equation

HRID 358679 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:18][C:19]([C:21]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:22]=1[N:23]([CH3:26])[CH:24]=O)=[O:20]>ClCCl>[C:1]([O:9][C:18]1[C:19](=[O:20])[C:21]2[C:22](=[CH:27][CH:28]=[C:29]([F:31])[CH:30]=2)[N:23]([CH3:26])[CH:24]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 23128095N-[2-(Chloroacetyl)-4-fluorophenyl]-N-methylformamide

Product 1

HCID 542187166-Fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzoic acid (6.7 g) and triethylamine (9.9 ml) in dichloromethane (80 ml) was added to the solution of 2'-(2-chloroacetyl)-4'-fluoro-N-methylformanilide at 0°. The mixture was stirred at ambient temperature for 24 hours and then heated under reflux for 2 hours. The mixture was washed with water (2×50 ml) and dried over magnesium sulphate. The solvent was removed by distillation and the residue added to potassium carbonate (1.76 g) and dry dimethylformamide (30 ml). The mixture was heated under nitrogen at 60° for 6 hours. Further potassium carbonate (1.0 g) was added and the heating continued for 6 hours. The solvent was removed under reduced pressure at 60° C., the residue triturated with water (30 ml), and the solid collected by filtration to give the novel compound 6-fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate, m.p. ]88°-190°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. washThe mixture was washed with water (2×50 ml)
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed by distillation
  6. additionthe residue added to potassium carbonate (1.76 g) and dry dimethylformamide (30 ml)
  7. temperatureThe mixture was heated under nitrogen at 60° for 6 hours
  8. additionFurther potassium carbonate (1.0 g) was added
  9. waitthe heating continued for 6 hours
  10. customThe solvent was removed under reduced pressure at 60° C.
  11. customthe residue triturated with water (30 ml)
  12. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-845969c5dcb34778a524f94f29c811c1
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

Loading…