Trifluoroacetic acid → HCID 59398023, compound

HRID 39698Notes

Reaction equation

HRID 39698 reaction equation
[CH:1]1([O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([CH3:22])=[CH:10][C:11](=[O:21])[N:12]3[CH2:15][CH:16]3OCC[O:17]3)=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].[OH-].[Na+]>O.C(OCC)(=O)C>[CH:1]1([O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([CH3:22])=[CH:10][C:11](=[O:21])[N:12]3[CH2:15][CH:16]=[O:17])=[CH:7][CH:6]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59398278HCID 59398278, compound

Product 1

HCID 59398023HCID 59398023, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 95 mg of 7-(cyclopropoxy)-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1H)-one, 1.5 mL of an 80% aqueous trifluoroacetic acid solution was added, the mixture was stirred at room temperature for 6 hours, and then stood still at room temperature for 14 hours. Thereto were added ethyl acetate and water, and the mixture was neutralized with an aqueous saturated sodium hydrogen carbonate solution and an aqueous sodium hydroxide solution. The organic layer was separated, 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 84 mg of a yellow oily substance, (7-(cyclopropoxy)-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde.

Workup

  1. waitstood still at room temperature for 14 hours
  2. customThe organic layer was separated
  3. washwashed sequentially with water
  4. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f6506e59d57740879b99cbf6379f5255
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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