HCID 20296308, compound → 5-(3-Methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:16]([O:18]C)=[O:17])[C:12](=[O:15])[NH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.Cl.C(O)(=O)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[NH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1Participants
3
Procedure
Methyl 1,2-dihydro-5-(3-methoxyphenyl)-2-oxo-3-pyridinecarboxylate is treated with 1:1 hydrochloric acid-acetic acid to give 1,2-dihydro-5-(3-methyoxyphenyl)-2-oxo-3-pyridinecarboxylic acid. This product is boiled in quinoline to afford 5-(3-methoxyphenyl)-2(1H)-pyridinone as the product. Treatment of this product with phosphorus oxychloride provides 2-chloro-5-(3-methoxyphenyl)pyridine. The preceding product is treated with hydrazine to produce 2-hydrazino-5-(3-methoxyphenyl)pyridine. Treatment of this product with ethyl orthoacetate yields 6-(3-methoxyphenyl)-3-methyl-1,2,4-triazolo[4,3-a]pyridine. Hydrogenation of the above product gives the product of the Example.
Sources & evidence
- ORD record
- ord-0fe3ed1dd98a47efbbab17455927a616
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04244953
Reaction notes
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