Trifluoroacetic acid → 7-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one

HRID 2193075Notes

Reaction equation

HRID 2193075 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=4)[C:16]([CH3:25])=[CH:15][C:14]3=[O:26])[CH2:7][CH2:6]2)[O:4]CC1.FC(F)(F)C(O)=O>C(O)C>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17]([C:16]([CH3:25])=[CH:15][C:14](=[O:26])[N:13]2[CH2:12][CH2:11][CH:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593979561-(2-(1,4-Dioxaspiro[4.5]decan-8-yl)ethyl)-7-methoxy-4-methylquinolin-2(1h)-one

Product 1

HCID 593978507-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.5 mL of an ethanol solution containing 65 mg of 1-(2-(1,4-dioxaspiro[4.5]decan-8-yl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one, 0.5 mL of an 80% aqueous trifluoroacetic acid solution was added under cooling with ice, and the mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, and water and ethyl acetate were added thereto. The reaction mixture was adjusted to pH 7.7 with an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 48 mg of a colorless oily substance, 7-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. customThe solvent was removed under reduced pressure, and water and ethyl acetate
  4. additionwere added
  5. customThe organic layer was separated
  6. washwashed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3d7ace5e747544839984ea7ec2827031
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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