Methanesulfonic Acid → 4-Chloro-6-methoxyquinolin-7-ol

HRID 1375769Notes

Reaction equation

HRID 1375769 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:19])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])C1C=CC=CC=1.C1(SC)C=CC=CC=1.CS(O)(=O)=O>FC(F)(F)S(O)(=O)=O>[Cl:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:20][CH3:21])[CH:11]=2)[N:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 7520ThioanisoleHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

HCID 1355837314-Chloro-6-methoxyquinolin-7-olYield 75.8%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

7-(Benzyloxy)-4-chloro-6-methoxyquinoline (100 mg), thioanisole (300 μl), and methanesulfonic acid (25 μl) were dissolved in trifluoromethanesulfonic acid (1 ml). The solution was stirred at room temperature for 30 min. The solvent was removed by distillation under the reduced pressure. The residue was made neutral by the addition of an aqueous sodium hydroxide solution, and hexane was added thereto to prepare a suspension. The crystal was collected by suction filtration to give 53 mg (yield 75%) of the title compound.

Workup

  1. customThe solvent was removed by distillation under the reduced pressure
  2. additionThe residue was made neutral by the addition of an aqueous sodium hydroxide solution, and hexane
  3. additionwas added
  4. customto prepare a suspension
  5. filtrationThe crystal was collected by suction filtration

Sources & evidence

ORD record
ord-8664bd8bc62a48d0bac85bc1ae2fc2b3
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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