2-Methoxyethanol → 1,4-Dihydro-7-(2-methoxyethoxy)-4-oxo-3-quinolinecarbonitrile

HRID 1837350Notes

Reaction equation

HRID 1837350 reaction equation
[H-].[Na+].F[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([OH:16])=[C:9]([C:14]#[N:15])[CH:10]=[N:11]2)=[CH:6][CH:5]=1.[CH3:17][O:18][CH2:19][CH2:20][OH:21]>>[CH3:17][O:18][CH2:19][CH2:20][O:21][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:16])[C:9]([C:14]#[N:15])=[CH:10][NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydride3×HCID 1785103157-Fluoro-4-hydroxyquinoline-3-carbonitrile

Product 1

HCID 102638471,4-Dihydro-7-(2-methoxyethoxy)-4-oxo-3-quinolinecarbonitrile

Procedure

A mixture of sodium hydride (500 mg, 12.5 mmol) and 7-fluoro-4-hydroxyquinoline-3-carbonitrile (1.30 g, 6.9 mmol) in 2-methoxyethanol (30 mL) is heated at reflux overnight. Additional sodium hydride (250 mg, 6.25 mmol) is added and the reaction mixture is heated at reflux overnight. Additional sodium hydride (250 mg, 6.25 mmol) is added and the reaction mixture is heated at reflux for 8 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The basic layer is acidified with aqueous HCl and the resultant solid is collected by filtration to provide 1.05 g of 7-(2-methoxyethoxy)-4-oxo-1,4-dihydroquinoline-3-carbonitrile as a white solid, mp>250° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux overnight
  5. temperaturethe reaction mixture is heated
  6. temperatureat reflux for 8 hours
  7. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  8. filtrationthe resultant solid is collected by filtration

Sources & evidence

ORD record
ord-883fe8d6d6b64ea39560827609d4a00b
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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