Trifluoroacetic acid → (7-Cyclohexyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde

HRID 2193067Notes

Reaction equation

HRID 2193067 reaction equation
[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([CH3:24])=[CH:12][C:13](=[O:23])[N:14]3[CH2:17][CH:18]3OCC[O:19]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>O>[CH:1]1([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([CH3:24])=[CH:12][C:13](=[O:23])[N:14]3[CH2:17][CH:18]=[O:19])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59398084HCID 59398084, compound

Product 1

HCID 59397891(7-Cyclohexyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.31 g of 7-cyclohexyl-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1H)-one, 10 mL of a 80% aqueous trifluoroacetic acid solution was added, the mixture was stirred at room temperature for 2 hours and then stood still at room temperature for 15 hours. Thereto were added ethyl acetate and water, and the reaction mixture was adjusted to pH 7.5 with an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.11 g of a colorless oily substance, (7-cyclohexyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde.

Workup

  1. waitstood still at room temperature for 15 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed sequentially with water
  5. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dc431be3e8084208a5419f2dbcc86c5d
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

Loading…