Acetic Acid → 2-(7-Chloro-6-fluoroquinolin-2-yl)methoxy-11-hydroxy-8-(2-acetylethyl)-6,11-dihydrodibenz[b,e]oxepine

HRID 232885Notes

Reaction equation

HRID 232885 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH2:19][O:20][C:21]3[CH:47]=[CH:46][C:24]4[O:25][CH2:26][C:27]5[CH:40]=[C:39]([CH2:41][CH2:42][C:43](=[O:45])[CH3:44])[CH:38]=[CH:37][C:28]=5[CH:29]([O:30]C5CCCCO5)[C:23]=4[CH:22]=3)=[N:16]2)=[CH:11][C:10]=1[F:48].C(O)(=O)C>O1CCOCC1.O>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH2:19][O:20][C:21]3[CH:47]=[CH:46][C:24]4[O:25][CH2:26][C:27]5[CH:40]=[C:39]([CH2:41][CH2:42][C:43](=[O:45])[CH3:44])[CH:38]=[CH:37][C:28]=5[CH:29]([OH:30])[C:23]=4[CH:22]=3)=[N:16]2)=[CH:11][C:10]=1[F:48]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 233591482-(7-Chloro-6-fluoroquinolin-2-yl)methoxy-8-(2-acetylethyl)-11-(2-tetrahydropyranyloxy)-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 233591362-(7-Chloro-6-fluoroquinolin-2-yl)methoxy-11-hydroxy-8-(2-acetylethyl)-6,11-dihydrodibenz[b,e]oxepineYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.02 ml of trifluoroacetic acid was added to 0.73 g of 2-(7-chloro-6-fluoroquinolin-2-yl)methoxy-8-(2-acetylethyl)-11-(2-tetrahydropyranyloxy)-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 74 dissolved in a mixed solution of 5 ml of dioxane and 2 ml of water, the mixture was stirred at room temperature for 15 minutes, 4 ml of acetic acid was added to the mixture and the mixture was stirred for 10 hours. 80 ml of water was added to the reaction mixture and insolubles were removed by filtration. The residue was dissolved in chloroform and the organic layer was washed with water and dried over anhydrous sodium sulfate. After the solvent was removed, the residue was washed with a mixed solution of acetone and ether to obtain 0.41 g of the title compound.

Workup

  1. customobtained in Reference example 74
  2. stirringthe mixture was stirred for 10 hours
  3. customwere removed by filtration
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter the solvent was removed
  8. washthe residue was washed with a mixed solution of acetone and ether

Sources & evidence

ORD record
ord-ba4536a181754e39a127951667b20ab4
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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