Ammonium Hydroxide → 7-Fluoro-1,4-dihydro-6-methoxy-4-oxo-3-quinolinecarboxamide

HRID 1837327Notes

Reaction equation

HRID 1837327 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12](O)=[O:13])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:16][CH3:17].[OH-].[NH4+:19]>CN(C)C=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]([NH2:19])=[O:13])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 12150700HCID 12150700, compound

Product 1

HCID 121507017-Fluoro-1,4-dihydro-6-methoxy-4-oxo-3-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (1.0 g, 4.21 mmol) and N,N′-carbonyldiimidazole (1.51 g, 9.28 mmol) in 14 mL of N,N-dimethylformamide is heated at 65° C. for 2 hours then cooled to room temperature and poured into 200 mL of aqueous ammonium hydroxide in an ice water bath. The solution is allowed to stir at room temperature overnight and then concentrated to a small volume. Ice cold water is added followed by acidification with acetic acid. The resultant solid is collected by filtration washing with water to provide 821 mg of 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxamide as a white solid, mp>300° C.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated to a small volume
  3. additionIce cold water is added
  4. filtrationThe resultant solid is collected by filtration
  5. washwashing with water

Sources & evidence

ORD record
ord-6d188bf212c6462fbcd289b210e37b5a
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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