Water → HCID 20290822, compound

HRID 1413821Notes

Reaction equation

HRID 1413821 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH:9]=[C:8]2[CH3:14].[C:32](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:6]=[C:7]2[C:12]=1[N:11]([CH3:32])[C:10](=[O:13])[CH:9]=[C:8]2[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20290830HCID 20290830, compound

Product 1

HCID 20290822HCID 20290822, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-methoxy-4-methyl-6-[2,2,2-trifluoro-1-benzyloxy-1-(trifluoromethyl)ethyl]-2(1H)-quinolinone in dimethylformamide is added potassium carbonate and methyl iodide. The solution is stirred and heated until analysis by thin layer chromatography indicates the reaction is complete. The solution is cooled and added to water. The aqueous mixture is extracted with ether. The etheral solution is dried with anhydrous magnesium sulfate, filtered and evaporated at reduced pressure. The residual material is purified by chromatography on silicic acid to give 8-methoxy-1,4-dimethyl-6-[2,2,2-trifluoro-1-benzyloxy-1-(trifluoromethyl)ethyl]-2(1H)-quinolinone.

Workup

  1. temperatureheated until analysis by thin layer chromatography
  2. temperatureThe solution is cooled
  3. extractionThe aqueous mixture is extracted with ether
  4. dry with materialThe etheral solution is dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated at reduced pressure
  7. customThe residual material is purified by chromatography on silicic acid

Sources & evidence

ORD record
ord-1577cd07267e43429f57562d8a1815dc
Source dataset
uspto-grants-1981_02
Patent number
US04251534

Reaction notes

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