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

HRID 1925341Notes

Reaction equation

HRID 1925341 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.CS(O)(=O)=O>C(O)(C(F)(F)F)=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

4

Reactant 2

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

Product 1

HCID 1355837314-Chloro-6-methoxyquinolin-7-ol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 7-(benzyloxy)-4-chloro-6-methoxyquinoline (WO98/13350A1)(2.0 g, 6.67 mmol) in TFA (13 mL), was added methansulfonic acid (0.95 mL, 13.3 mmol). The mixture was heated to reflux for 3 h. After cooling to RT, the mixture was concentrated in vacuo. The resulting residue was diluted with ice/H2O and neutralized with cold 1N NaOH to a pH of 7. The resulting precipitate was stirred for 1 h at RT, filtered, and dried under high vacuum to give the title compound as a light yellow solid. MS (ESI, pos. ion) m/z: 210 (M+1). Mass Calc'd for C10H8ClNO2: 209.0.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe resulting residue was diluted with ice/H2O and neutralized with cold 1N NaOH to a pH of 7
  5. filtrationfiltered
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-310f53ab82b84c80b44cddb128a2d24c
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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