Boron trifluoride → Methyl 6-hydroxyquinoline-5-carboxylate

HRID 4790

Reaction equation

HRID 4790 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([OH:14])=[O:13].B(F)(F)F.[C:19](=O)(O)[O-].[Na+]>>[CH3:19][O:13][C:12]([C:3]1[C:4]2[CH:5]=[CH:6][CH:7]=[N:8][C:9]=2[CH:10]=[CH:11][C:2]=1[OH:1])=[O:14]

Participants

4

Reactant 3

HCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 160424816-Hydroxyquinoline-5-carboxylic acid

Product 1

HCID 19077292Methyl 6-hydroxyquinoline-5-carboxylate

Procedure

6-Hydroxy-5-quinolinecarboxylic acid [as reported by Da Re, P. et al. in Ann. Chem. (Rome) 1970, 60(3), 215-24 (C.A. 73, 25338m)] is reacted with methanolic boron trifluoride solution for several hours. The resulting mixture is added to an aqueous solution of sodium bicarbonate to give finally a basic solution. The solution is extracted with chloroform. The chloroform extract is dried over anhydrous sodium sulfate and concentrated and the residue is crystallized from a suitable solvent.

Workup

  1. customto give finally a basic solution
  2. extractionThe solution is extracted with chloroform
  3. extractionThe chloroform extract
  4. dry with materialis dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe residue is crystallized from a suitable solvent

Sources & evidence

ORD record
ord-c857701e44354b45bafe59192161b725
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Linked notes

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