2-Methoxyethanol → 1,4-Dihydro-6-methoxy-7-(2-methoxyethoxy)-4-oxo-3-quinolinecarbonitrile

HRID 1837331Notes

Reaction equation

HRID 1837331 reaction equation
[Na].[CH3:2][O:3][CH2:4][CH2:5][OH:6].F[C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:20])[C:13]([C:18]#[N:19])=[CH:14][NH:15]2)=[CH:10][C:9]=1[O:21][CH3:22]>C(O)(=O)C>[CH3:22][O:21][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:8]=1[O:6][CH2:5][CH2:4][O:3][CH3:2])[NH:15][CH:14]=[C:13]([C:18]#[N:19])[C:12]2=[O:20]

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 5360545SodiumHCID 121507027-FLUORO-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILE

Product 1

HCID 99705581,4-Dihydro-6-methoxy-7-(2-methoxyethoxy)-4-oxo-3-quinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium (84 mg, 3.67 mmol) is added to 3.6 mL of 2-methoxyethanol and the mixture is heated at reflux for 90 minutes. 7-Fluoro-6-methoxy-4-oxo-1,4,-dihydro-3-quinolinecarbonitrile (200 mg, 0.92 mmol) is added and the reaction mixture is heated at reflux for 4 hours then stirred at room temperature overnight. The reaction mixture is poured into ice water and acidified with acetic acid. The solids are collected by filtration, washing with ethyl acetate and hexane, to provide 234 mg of 6-methoxy-7-(2-methoxyethoxy)-4-oxo-1,4,-dihydro-3-quinolinecarbonitrile, mp>300° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 90 minutes
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 4 hours
  5. filtrationThe solids are collected by filtration
  6. washwashing with ethyl acetate and hexane

Sources & evidence

ORD record
ord-290ec1f075fa4aebb23c1a80664cbfa8
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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