Sodium hydride → HCID 5330112, compound

HRID 1837364Notes

Reaction equation

HRID 1837364 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1F)[N:11]=[CH:10][C:9]([C:16]#[N:17])=[C:8]2[NH:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1>COCCO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:27][CH2:22][CH2:23][O:25][CH3:26])[N:11]=[CH:10][C:9]([C:16]#[N:17])=[C:8]2[NH:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1

Participants

4

Reactant 2

HCID 24758Sodium hydride2×HCID 23498072HCID 23498072, compound

Product 1

HCID 5330112HCID 5330112, compoundYield 152.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of sodium hydride (80 mg, 2.0 mmol) and 6-methoxy-7-fluoro-4-[(3,4,5-tri-methoxyphenyl)amino]-3-quinolinecarbonitrile (203 mg, 0.53 mmol) in 2-methoxyethanol (6 mL) is heated at reflux for 2 hours. Additional sodium hydride (80 mg, 2.0 mmol) is added and the reaction mixture is heated at reflux for 4 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Trituration of the residue with ethyl acetate and diethyl ether provides 178 mg of 6-methoxy-7-[2-methoxyethoxy]-4-[(3,4,5-trimethoxyphenyl)amino]-3-quinolinecarbonitrile, mp 188-190° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 4 hours
  5. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78775ac3156a4a4e997bf782708f33f2
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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