Acetic Anhydride → 4-(5-Acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxyquinoline

HRID 393627Notes

Reaction equation

HRID 393627 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].Cl.[CH2:9]([O:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21]([NH:27][C:28]3C=C(O)[C:31]([Cl:35])=[CH:30][C:29]=3[F:36])=[CH:22][CH:23]=[N:24]2)=[CH:19][C:18]=1[O:37][CH3:38])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C)C1C=CN=CC=1>[C:5]([O:4][C:1]1[C:31]([Cl:35])=[CH:30][C:29]([F:36])=[C:28]([CH:2]=1)[NH:27][C:21]1[C:20]2[C:25](=[CH:26][C:17]([O:16][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[C:18]([O:37][CH3:38])[CH:19]=2)[N:24]=[CH:23][CH:22]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 226465807-Benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxyquinoline hydrochloride

Product 1

HCID 226465634-(5-Acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxyquinolineYield 102.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-Dimethylaminopyridine (12 mg, 0.1 mmol) and acetic anhydride (122 mg, 1.2 mmol) were added to a suspension of 7-benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxyquinoline hydrochloride (461 mg, 1 mmol), (prepared as described in Example 12). The mixture was heated at reflux for 1 hour and the volatiles were removed by evaporation. The residue was triturated with water and the resulting precipitate was collected by filtration and dried under vacuum to give 4-(5-acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxyquinoline (480 mg, 95%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthe volatiles were removed by evaporation
  4. customThe residue was triturated with water
  5. filtrationthe resulting precipitate was collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-de7ab90340664933ac3f243f1dff70ed
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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