Boron trifluoride → Methyl 6-hydroxyquinoline-5-carboxylate

반응식

[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]

참가 물질

반응물 3

HCID 6356Boron trifluoride

HCID 516892Sodium Bicarbonate

HCID 160424816-Hydroxyquinoline-5-carboxylic acid

생성물 1

HCID 19077292Methyl 6-hydroxyquinoline-5-carboxylate

실험 절차

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.