Potassium Carbonate → HCID 68631337, compound

HRID 1750131Notes

Reaction equation

HRID 1750131 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Cl:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17]Cl.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Cl:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6421971,4-Dichloro-2-butene, (2E)-HCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 68631337HCID 68631337, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (196 mg, 1.2 mmol), (E)-1,4-dichlorobut-2-ene (450 mg, 3.6 mmol) and anhydrous K2CO3 (166 mg, 1.2 mmol) was dissolved in EtOH and the solution was heated to reflux and stirred overnight. The solution was diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated aq NaHCO3, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column to give (E)-7-(4-chlorobut-2-enyloxy)-3,4-dihydroquinolin-2(1H)-one (intermediate 52) (102 mg, 34%) as a white solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with saturated aq NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel column

Sources & evidence

ORD record
ord-cbe5b489df314b3a8141316982b40c3b
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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