7-Benzyloxy-4-chloro-6-methoxyquinoline hydrochloride → 4-Chloro-6-methoxyquinolin-7-ol

HRID 393598Notes

Reaction equation

HRID 393598 reaction equation
Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:20][C:14]1[C:13]2[C:18](=[CH:19][C:10]([OH:9])=[C:11]([O:21][CH3:22])[CH:12]=2)[N:17]=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 226465617-Benzyloxy-4-chloro-6-methoxyquinoline hydrochloride

Product 1

HCID 1355837314-Chloro-6-methoxyquinolin-7-olYield 98%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-chloro-6-methoxyquinoline hydrochloride (6.8 g, 20 mmol) in TFA (80 ml) was heated at reflux for 5.5 hours. The volatiles were removed by evaporation, the residue suspended in water and the mixture was adjusted to pH7 with a saturated aqueous sodium hydrogen carbonate solution. The resulting solid was collected by filtration, washed with water, ether and dried under vacuum to give 4-chloro-7-hydroxy-6-methoxyquinoline (4.1 g, 98%).

Workup

  1. temperatureat reflux for 5.5 hours
  2. customThe volatiles were removed by evaporation
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water, ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a07b263e1f9c44569f87333c7a7d219b
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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