Trifluoroacetic acid → HCID 59398121, compound

HRID 2193090Notes

Reaction equation

HRID 2193090 reaction equation
FC(F)(F)C(O)=O.[O:8]1CCO[CH:9]1[CH2:13][N:14]1[C:23]2[CH:22]=[C:21]([O:24][CH3:25])[CH:20]=[C:19]([C:26]([O:28][CH3:29])=[O:27])[C:18]=2[CH:17]=[CH:16][C:15]1=[O:30]>>[CH3:25][O:24][C:21]1[CH:20]=[C:19]([C:26]([O:28][CH3:29])=[O:27])[C:18]2[CH:17]=[CH:16][C:15](=[O:30])[N:14]([CH2:13][CH:9]=[O:8])[C:23]=2[CH:22]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398314HCID 59398314, compound

Product 1

HCID 59398121HCID 59398121, compound

Procedure

Into 5 mL of a 90% aqueous trifluoroacetic acid solution, 350 mg of methyl 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-5-carboxylate was dissolved, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the resultant solution was alkalified with an aqueous saturated sodium hydrogen carbonate solution, and then extracted with ethyl acetate. The organic layer 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 476 mg of a pale yellow oily substance, methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-5-carboxylate.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed 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-de27016453b546a2be24db8506783dc0
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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