Trifluoroacetic acid → HCID 59398036, compound

HRID 39843Notes

Reaction equation

HRID 39843 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10](/[CH:19]=[CH:20]/[C:21]([NH2:23])=[O:22])=[CH:9][C:8]1=[O:24].FC(F)(F)C(O)=O>>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11]([C:10](/[CH:19]=[CH:20]/[C:21]([NH2:23])=[O:22])=[CH:9][C:8](=[O:24])[N:7]2[CH2:6][CH:2]=[O:1])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398025HCID 59398025, compound

Product 1

HCID 59398036HCID 59398036, compoundYield 56.5%

Procedure

To 0.20 g of (2E)-3-(1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)-acrylamide, 5 mL of 80% aqueous trifluoroacetic acid solution was added, and stirred at room temperature for 4 hours, thereafter allowed to stand at the same temperature overnight. After the solvent was removed under reduced pressure, water was added and adjusted to pH 7.8 with 1.0 mol/L aqueous sodium hydroxide solution. The resulting solid was filtered to give 98 mg of (2E)-3-(7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinolin-4-yl)acrylamide as a light brown solid.

Workup

  1. customto stand at the same temperature overnight
  2. customAfter the solvent was removed under reduced pressure, water
  3. additionwas added
  4. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-a6d83b48ec6943c299d5c9e5f872051e
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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