4-Hydroxymethyl-1-(3-chlorophenyl)-1H-pyridin-2-one → 1-(3-Chloro-phenyl)-2-oxo-1,2-dihydro-pyridine-4-carbaldehyde
Reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[C:5](=[O:16])[CH:4]=1>C(Cl)Cl.O=[Mn]=O>[Cl:15][C:11]1[CH:10]=[C:9]([N:6]2[CH:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][C:5]2=[O:16])[CH:14]=[CH:13][CH:12]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-hydroxymethyl-1-(3-chlorophenyl)-1H-pyridin-2-one (2.39 g, 10.14 mmol) in CH2Cl2 (250 ml) was added MnO2 (4.41 g, 50.71 mmol) and stirred for 18 hours. The suspension was filtered through celite and the pad washed with additional CH2Cl2 (200 ml). The combined filtrates were evaporated in vacuo and chromatographed (silica gel, 5-20% EtOAc: CH2Cl2 gradient elution) to afford the title compound.