5-(4-Methoxyphenyl)-3,6-dimethyl-3,4-dihydropyridin-2(1H)-one → HCID 53807414, compound
Reaction equation
[CH3:1][CH:2]1[CH2:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[C:5]([CH3:16])[NH:4][C:3]1=[O:17]>C(O)(=O)C.[Pt](Cl)Cl>[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH:5]([CH3:16])[NH:4][C:3]1=[O:17]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1 g of platinum chloride was added to a solution of 15 g (65 mmol) of 3,6-dimethyl-5-(4-methoxyphenyl)-3,4-dihydro-2-pyridone (Synthesis 305, 1985) in 75 ml of glacial acetic acid and the mixture was hydrogenated at room temperature and a pressure of 52 psi for 8 hours. The catalyst was then removed by filtration and the glacial acetic acid was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed successively with ammonia (5%), water and a saline solution. The organic layer was dried on sodium sulphate, filtered and evaporated under reduced pressure. The resulting crude product (15 g) was purified chromatographically over a dry column of 700 g of silcagel (Merck, grain size 0.063-0.200 mm) using a mixture of dichloromethane and acetone (95:5) as an eluent. After evaporating the correct fractions, 5.8 g (38%) of the desired 3,6-dimethyl-5-(4-methoxyphenyl)-3,4,5,6-tetrahydro-2-pyridone were obtained in addition to 3.5 g (23%) of the starting compound.