Ethyl Bromide → 3-Quinolinecarboxylic acid, 7-amino-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-

HRID 1583548Notes

Reaction equation

HRID 1583548 reaction equation
[CH2:1](Br)[CH3:2].C([NH:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:23])=[C:13]([C:18]([O:20]CC)=[O:19])[CH:14]=[N:15]2)=[CH:10][C:9]=1[F:24])(=O)C>O.C(O)C.[OH-].[Na+]>[F:24][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:8]=1[NH2:7])[N:15]([CH2:1][CH3:2])[CH:14]=[C:13]([C:18]([OH:20])=[O:19])[C:12]2=[O:23]

Participants

6

Reactant 2

HCID 6332Ethyl BromideHCID 178469624HCID 178469624, compound

Product 1

HCID 6098843-Quinolinecarboxylic acid, 7-amino-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.5 ml of ethyl bromide is added to a solution of 1 gram of ethyl 7-acetamido-4-hydroxy-6-fluoro-3-quinolinecarboxylate in 25 ml of water, 60 ml of ethanol and 2.5 ml of 10% sodium hydroxide solution, and the mixture is maintained under reflux for 4 hours. The mixture is then concentrated to half its volume, 5 ml of 10% sodium hydroxide solution are added and refluxing is maintained for 1 hour. The mixture is allowed to cool and is acidified with hydrochloric acid, and the precipitate formed is filtered off. The precipitate is washed with water, dried, and recrystallized in a dimethylformamide/water (10:1) mixture.

Workup

  1. temperaturethe mixture is maintained
  2. temperatureunder reflux for 4 hours
  3. concentrationThe mixture is then concentrated to half its volume, 5 ml of 10% sodium hydroxide solution
  4. additionare added
  5. temperaturerefluxing
  6. temperatureis maintained for 1 hour
  7. temperatureto cool
  8. customthe precipitate formed
  9. filtrationis filtered off
  10. washThe precipitate is washed with water
  11. customdried
  12. customrecrystallized in a dimethylformamide/water (10:1) mixture

Sources & evidence

ORD record
ord-ea40e897199e423d8ac434d5a76f5253
Source dataset
uspto-grants-1985_11
Patent number
US04552882

Reaction notes

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