7-Benzyloxy-4-(4-chloro-2-fluoroanilino)-6-methoxyquinoline hydrochloride → 4-(4-Chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinoline

HRID 393647ノート

反応式

HRID 393647 の反応式
Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[F:28])=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:29][CH3:30])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:14]2[C:13]3[C:18](=[CH:19][C:10]([OH:9])=[C:11]([O:29][CH3:30])[CH:12]=3)[N:17]=[CH:16][CH:15]=2)=[C:22]([F:28])[CH:23]=1

参加物

3

反応物 1

HCID 226465997-Benzyloxy-4-(4-chloro-2-fluoroanilino)-6-methoxyquinoline hydrochloride

生成物 1

HCID 1358046894-(4-Chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinoline収率 85.6%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

A mixture of 7-benzyloxy-4-(4-chloro-2-fluoroanilino)-6-methoxyquinoline hydrochloride (4.7 g, 11 mmol), (prepared as described in Example 41), in TFA (100 ml) was heated at reflux for 4 hours. The volatiles were removed by evaporation. Saturated aqueous sodium hydrogen carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The combined extracts were dried (MgSO4), and the solvent was removed by evaporation. The residue was dissolved in methanol, aqueous ammonia was added and the mixture was stirred for 1 hour. The volatiles were removed by evaporation and the residue was diluted with water. The precipitated product was collected by filtration, washed with water and dried to give 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinoline (3 g, 76%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe volatiles were removed by evaporation
  4. additionSaturated aqueous sodium hydrogen carbonate solution was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customthe solvent was removed by evaporation
  8. dissolutionThe residue was dissolved in methanol
  9. additionaqueous ammonia was added
  10. customThe volatiles were removed by evaporation
  11. additionthe residue was diluted with water
  12. filtrationThe precipitated product was collected by filtration
  13. washwashed with water
  14. customdried

出典と根拠

ORDレコード
ord-8b4d6ade3dfc405c83cda8cff29a4d25
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

反応ノート

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