Quinoline → HCID 178516370, compound

HRID 503499Notes

Reaction equation

HRID 503499 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:15])=[C:7](C(O)=O)[CH:8]=[N:9]2)=[N:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1>CC(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:15])=[CH:7][CH:8]=[N:9]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 178524700HCID 178524700, compound

Product 1

HCID 178516370HCID 178516370, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a RBF fitted with a reflux condenser, 7-bromo-4-hydroxy-1,5-naphthyridine-3-carboxylic acid (1 g, 4 mmol) was added in portions over 10 minutes to stirred refluxing quinoline (50 mL), and the resulting mixture was refluxed for 1 h. The mixture was cooled and diluted with acetone. The precipitate was filtered, washed with water and dried to give 0.8 g of a grey-brown powder. The product was reprecipitated from aq. NaOH with glacial acetic acid to give a white solid.

Workup

  1. customIn a RBF fitted with a reflux condenser
  2. temperaturethe resulting mixture was refluxed for 1 h
  3. temperatureThe mixture was cooled
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ae83a504a2634e90974b367c7895202f
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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