Sodium Hydroxide → 4-Methyl-3-(1-methylphthalazin-6-yl)benzoic acid

Reaction equation

[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([CH3:23])=[N:18][N:17]=[CH:16]2.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([CH3:23])=[N:18][N:17]=[CH:16]2

Participants

Procedure

A solution of ethyl 4-methyl-3-(1-methylphthalazin-6-yl)benzoate (51.7 mg, 169 μmol) in tetrahydrofuran (800 μl) and methanol (400 μl) was added 1N aqueous sodium hydroxide solution (338 μl, 338 μmol) and stirred at RT for 18 h. The reaction was concentrated in vacuo and the residue was taken up in water and the pH was adjusted with 10% aqueous HCl solution to ˜7. The aqueous mixture was extracted with 15% MeOH/CHCl3 (3×) and the organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo to give 4-methyl-3-(1-methylphthalazin-6-yl)benzoic acid as a maize solid. MS (ES+): 279.1 (M+H)+.