Potassium Hydroxide → 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylic Acid

HRID 52009Notes

Reaction equation

HRID 52009 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]=2[C:22]([O:24]C)=[O:23])[N:4]=1.[OH-].[K+]>CO.COCC>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]=2[C:22]([OH:24])=[O:23])[N:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19962792Methyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylate

Product 1

HCID 199627686-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylic AcidYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10903MethoxyethaneSolvent

Procedure

0.8 g of methyl 6-[(4,6-dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylate was dissolved in 10 ml of methanol and 20 ml of methoxyethane, and 5 ml of an aqueous solution containing 0.39 g of potassium hydroxide was added thereto at 40° C. The mixture was extracted with dichloromethane. The aqueous layer was acidified (pH=4) with a 10% hydrochloric acid aqueous solution, and formed precipitates were collected by filtration and dried to obtain 0.5 g (yield: 66.0%) of the desired compound. mp: 195°-198° C.

Workup

  1. additionwas added
  2. customat 40° C
  3. extractionThe mixture was extracted with dichloromethane
  4. customformed
  5. customprecipitates
  6. filtrationwere collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-a7e005a830614afb9b89fc4e29f8401d
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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