Sodium Hydroxide → 6-Aminoquinoline-5-carboxylic acid

Reaction equation

C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[CH:12]=[CH:13][C:14]=1[NH2:15])=[O:4].[OH-].[Na+]>O1CCOCC1.CO>[NH2:15][C:14]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]=1[C:3]([OH:4])=[O:2]

Participants

Procedure

To a solution of 540 mg (2.19 mmol) of the above 6-amino-quinoline-5-carboxylic acid methyl ester in 10.8 mL of dioxane and 0.54 mL of methanol is added 5.48 mL (5.48 mmol) of an aqueous solution of NaOH 1N. The reaction is stirred 24 hours at ambient temperature. Then the solvents are evaporated in vacuo and the residue is suspended in a minimum of water and precipitated at pH 6 by addition of concentrated HCl. After filtration and washing with a minimum of water the solid obtained is dried on high vacuum pump to give 245 mg (60%) of a yellowish solid; LC/MS:189/190 (M+H)+.