Acetic Acid → 6-Bromo-2-pyridin-2-ylquinoline-4-carboxylic acid

HRID 2224571

Reaction equation

HRID 2224571 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)(=O)[CH3:14].CC[OH:24].CC(O)=O>[OH-].[K+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH:14]=[C:5]2[C:6]([OH:11])=[O:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 68895-BromoisatinHCID 142862-Acetylpyridine

Product 1

HCID 7591236-Bromo-2-pyridin-2-ylquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

To a suspension of 5-bromo isatin (5 g, 20.5 mmol) and 2-acetylpyridine (2.5 g, 20.5 mmol) in aqueous KOH (1.2 g, 33%) was added EtOH until a solution formed. The mixture was refluxed over night. The reaction mixture was neutralized with HOAc (50%) and filtered. The solid was resuspended in EtOH and filtered to give the title compound (5.5 g). LC: 1.66 and MH+: 329.

Workup

  1. customformed
  2. temperatureThe mixture was refluxed over night
  3. filtrationfiltered
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8f4ff10bb5ec4d08a309adc68380f0ff
Source dataset
uspto-grants-2008_05
Patent number
US07378430B2

Linked notes

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