Hydrochloric Acid → 7-Fluoro-4-hydroxy-1-(2-propen-1-yl)-2(1H)-quinolinone

HRID 657120Notes

Reaction equation

HRID 657120 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:21])=[C:7](C(OCC)=O)[C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[CH2:14])=[CH:4][CH:3]=1.Cl>[OH-].[Na+]>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:21])=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[CH2:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68994561Ethyl 7-fluoro-4-hydroxy-2-oxo-1-(2-propen-1-yl)-1,2-dihydro-3-quinolinecarboxylate

Product 1

HCID 688207057-Fluoro-4-hydroxy-1-(2-propen-1-yl)-2(1H)-quinolinoneYield 81.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 7-fluoro-4-hydroxy-2-oxo-1-(2-propen-1-yl)-1,2-dihydro-3-quinolinecarboxylate (4.46 g, 15.3 mmol) was suspended in 2N sodium hydroxide solution (70 ml) and heated at reflux for 4 h. After cooling, the pH was adjusted to ˜pH6 using 2N hydrochloric acid and the resulting precipitate filtered off, washed with water and dried under vacuum to provide the title compound as an off-white solid (2.73 g, 81%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. temperatureAfter cooling
  4. filtrationthe resulting precipitate filtered off
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b1937b4373b142ffbe38cde718e3646d
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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