Potassium Carbonate → HCID 66633798, compound

HRID 1750128Notes

Reaction equation

HRID 1750128 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][C:15]#[C:16][CH2:17]Cl.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Cl:13][CH2:14][C:15]#[C: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 131821,4-Dichloro-2-butyneHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 66633798HCID 66633798, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (930 mg, 6 mmol), 1,4-dichlorobut-2-yne (326 mg, 2 mmol) and anhydrous K2CO3 (276 mg, 2 mmol) was dissolved in EtOH and the solution was heated to reflux 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 7-(4-chlorobut-2-ynyloxy)-3,4-dihydroquinolin-2(1H)-one (intermediate 50) (330 mg, 66%) as a yellow solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  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-9e7f782c60a248ee9df520da853abfa4
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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