3,5-Dimethoxyisonicotinaldehyde → 3-Hydroxy-5-methoxyisonicotinaldehyde
Reaction equation
C[O:2][C:3]1[CH:10]=[N:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=[O:6].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[OH:2][C:3]1[CH:10]=[N:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,5-dimethoxyisonicotinaldehyde (2.7 g, 16.16 mmol, 1 eq.) in DCM (100 mL) was added AlCl3 (4.31 g, 32.32 mmol, 2.0 eq.) at rt. The mixture was reflux O/N, cooled to rt, and added into ice (200 g). The aqueous layer was extracted with DCM three times. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 3-hydroxy-5-methoxyisonicotinaldehyde (420 mg, 17%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 10.96 (s, 1H), 10.26 (s, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 3.84 (s, 3H). LRMS (M+H+) m/z 154.1.