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

HRID 2193068Notes

Reaction equation

HRID 2193068 reaction equation
[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([C:8]([CH3:21])=[CH:9][C:10](=[O:20])[N:11]3[CH2:14][CH:15]3OCC[O:16]3)=[CH:6][CH:5]=2)[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:4]2[CH:13]=[C:12]3[C:7]([C:8]([CH3:21])=[CH:9][C:10](=[O:20])[N:11]3[CH2:14][CH:15]=[O:16])=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59398150HCID 59398150, compound

Product 1

HCID 59398306(7-Cyclopropyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.10 g of 7-cyclopropyl-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1H)-one, 3 mL of an 80% aqueous trifluoroacetic acid solution was added, the mixture was stirred at room temperature for 1 hour, and then stood still at room temperature for 13 hours. Thereto were added 3 mL of ethyl acetate and 4 mL of water, and the mixture was neutralized with an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 59 mg of a light brown oily substance, (7-cyclopropyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde.

Workup

  1. waitstood still at room temperature for 13 hours
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ef3089abe8d64738b82e7bd4503d7b54
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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