Methyl iodide → 6,7,8-Trifluoro-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxylic acid

HRID 434564ノート

反応式

HRID 434564 の反応式
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([F:19])[C:11]([F:18])=[C:12]([F:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])C.[C:20](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[F:17][C:12]1[CH:13]=[C:14]2[C:9](=[C:10]([F:19])[C:11]=1[F:18])[N:8]([CH3:20])[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[C:15]2=[O:16]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27339723-Quinolinecarboxylic acid, 1,4-dihydro-4-oxo-6,7,8-trifluoro-, ethyl ester

生成物 1

HCID 127708996,7,8-Trifluoro-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxylic acid収率 77.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester (0.3 g), anhydrous potassium carbonate (0.8 g), methyl iodide (1.6 g), and N,N-dimethyl-formamide (DMF) (10 ml) was heated with stirring at 90°-100° C. for 10 hours. The mixture was evaporated to dryness. The residue was treated with water, extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was added to a mixture of 18% hydrochloric acid (5 ml) and ethanol (2.5 ml) and the mixture was refluxed for 2.5 hours. After water (5 ml) and ethanol (5 ml) added and cooled, the resulting precipitate was filtered off and recrystallized from a mixture of DMF and ethanol to give 6,7,8-trifluoro-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxylic acid (0.22 g), mp 255°-258° C.

後処理

  1. temperaturewas heated
  2. customThe mixture was evaporated to dryness
  3. additionThe residue was treated with water
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. additionThe residue was added to a mixture of 18% hydrochloric acid (5 ml) and ethanol (2.5 ml)
  9. temperaturethe mixture was refluxed for 2.5 hours
  10. additionAfter water (5 ml) and ethanol (5 ml) added
  11. temperaturecooled
  12. filtrationthe resulting precipitate was filtered off
  13. customrecrystallized from a mixture of DMF and ethanol

出典と根拠

ORDレコード
ord-f30dea91d8904733aefa6b2dd8cc6106
出典データセット
uspto-grants-1983_08
特許番号
US04398029

反応ノート

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