Potassium Carbonate → HCID 58026816, compound

HRID 1966299Notes

Reaction equation

HRID 1966299 reaction equation
C([O:4][C:5]1[CH:36]=[CH:35][C:8]([C:9]([O:11][CH2:12][C:13]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[O:30][CH3:31])=[CH:21][CH:20]=[C:19]3[C:14]=2[C:15]([CH3:34])=[CH:16][C:17]([CH3:33])([CH3:32])[NH:18]3)=[O:10])=[CH:7][CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]2[C:13]([CH2:12][O:11][C:9](=[O:10])[C:8]3[CH:7]=[CH:6][C:5]([OH:4])=[CH:36][CH:35]=3)=[C:14]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([CH3:32])([CH3:33])[CH:16]=[C:15]3[CH3:34])=[C:24]([O:30][CH3:31])[CH:25]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58026980HCID 58026980, compound

Product 1

HCID 58026816HCID 58026816, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Acetoxybenzoyloxymethyl)-6-(4-fluoro-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 12-5, 40.9 mg, 0.0835 mmol) and potassium carbonate (24.0 mg, 0.174 mmol) were suspended in anhydrous methanol (1 mL), and the mixture was stirred at room temperature for 1.5 hours. After the unsoluble materials were filtered, the filtrate was concentrated under reduced pressure, and ethyl acetate (50 mL) and water (50 mL) were added thereto, and then separated. The organic layer was washed with water (30 mL) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was filtered with hexane to give the titled compound (28.8 mg) as a colorless solid. (Yield 78%)

Workup

  1. filtrationAfter the unsoluble materials were filtered
  2. concentrationthe filtrate was concentrated under reduced pressure, and ethyl acetate (50 mL) and water (50 mL)
  3. additionwere added
  4. customseparated
  5. washThe organic layer was washed with water (30 mL) and saturated brine (30 mL) successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. filtrationThe obtained residue was filtered with hexane

Sources & evidence

ORD record
ord-00e98fce38524138ae5dfc3633c333f2
Source dataset
uspto-grants-2013_04
Patent number
US08420635B2

Reaction notes

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