Water → 8-Fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate

HRID 358673ノート

反応式

HRID 358673 の反応式
S(Cl)(Cl)(=O)=O.[C:6]([C:9]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:10]=1[N:11]([CH3:14])[CH:12]=O)(=[O:8])[CH3:7].[OH2:20]>ClCCl>[C:6]([O:8][C:7]1[C:6](=[O:8])[C:9]2[C:10](=[C:15]([F:19])[CH:16]=[CH:17][CH:18]=2)[N:11]([CH3:14])[CH:12]=1)(=[O:20])[C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:10]=1

参加物

5

反応物 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 231281372'-acetyl-6'-fluoro-N-methylformanilide

生成物 1

HCID 544988888-Fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of sulphuryl chloride (11.9 ml) in dichloromethane (200 ml) was added dropwise to the solution of 2'-acetyl-6'-fluoro-N-methylformanilide at 0° under a nitrogen atmosphere. The reaction mixture was stirred at 0° for 3.25 hours. Water (100 ml) was added dropwise and the mixture stirred for 30 minutes. The dichloromethane layer was separated, washed with water (160 ml) and dried over magnesium sulphate before removing the solvent under reduced pressure at ambient temperature. The residue was added to a mixture of benzoic acid (22.6 g), potassium carbonate (42.5 g), 25 molecular sieves (4A°, 50 g) and dry dimethylformamide (200 ml) and the resultant mixture stirred at ambient temperature for 3 hours and then at 60° for 2 hours. Further dimethylformamide (600 ml) and potassium carbonate (17 g) were added and the mixture was heated at 60° overnight. The mixture was cooled, filtered and the solvent removed from the filtrate under reduced pressure at 60°. The residue was triturated with water (400 ml) and then with diethyl ether (400 ml). The resultant solid was crystallised from industrial methylated spirit (200 ml) to give the novel compound 8-fluoro-1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate, m.p. 179°-181°.

後処理

  1. stirringthe mixture stirred for 30 minutes
  2. customThe dichloromethane layer was separated
  3. washwashed with water (160 ml)
  4. dry with materialdried over magnesium sulphate
  5. custombefore removing the solvent under reduced pressure at ambient temperature
  6. additionThe residue was added to a mixture of benzoic acid (22.6 g), potassium carbonate (42.5 g), 25 molecular sieves (4A°, 50 g) and dry dimethylformamide (200 ml)
  7. stirringthe resultant mixture stirred at ambient temperature for 3 hours
  8. waitat 60° for 2 hours
  9. additionFurther dimethylformamide (600 ml) and potassium carbonate (17 g) were added
  10. temperaturethe mixture was heated at 60° overnight
  11. temperatureThe mixture was cooled
  12. filtrationfiltered
  13. customthe solvent removed from the filtrate under reduced pressure at 60°
  14. customThe residue was triturated with water (400 ml)
  15. customThe resultant solid was crystallised from industrial methylated spirit (200 ml)

出典と根拠

ORDレコード
ord-f4a9f5e6d6d841728cf3dcc5f7e75123
出典データセット
uspto-grants-1991_03
特許番号
US04997840

反応ノート

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