Potassium Carbonate → HCID 19592777, compound

HRID 613542Notes

Reaction equation

HRID 613542 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[C:8]([NH:13][C:14](=[O:23])[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[CH2:24][O:25][CH3:26].[C:27](=O)([O-])[O-:28].[K+].[K+]>COCCOC.CO>[CH3:26][O:25][CH2:24][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:3]=1[CH2:2][O:28][CH3:27])=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14](=[O:23])[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 19592558HCID 19592558, compound

Product 1

HCID 19592777HCID 19592777, compoundYield 27.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-chloromethyl-8-(2,6-dichlorobenzoylamino)-3-methoxymethylquinoline (70 mg) and potassium carbonate (26 mg) in 1,2-dimethoxyethane and methanol was refluxed for 2 hours. After cooling, the mixture was partitioned between saturated ammonium chloride solution and dichloromethane, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography and crystallized from isopropyl alcohol to give 3,4-bis(methoxymethyl)-8-(2,6-dichlorobenzoylamino)quinoline (19.2 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between saturated ammonium chloride solution and dichloromethane
  4. washthe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin layer chromatography
  8. customcrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-60c10582142948cf96986975f018d47e
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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