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

HRID 393647Notes

Reaction equation

HRID 393647 reaction equation
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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-8b4d6ade3dfc405c83cda8cff29a4d25
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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