2-(4-Fluorophenyl)acetic acid → HCID 54517698, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH3:12][N+:13]([CH3:16])=[CH:14]Cl.[Cl-]>>[CH3:12][N:13]([CH3:16])[CH:14]=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:9]=[O:11]Participants
Procedure
In a manner similar to Example 1, p-fluorophenyl acetic acid is treated with Vilsmeier reagent to produce 3-(dimethylamino)-2-(4-fluorophenyl)-2-propenal. Treatment of this product with cyanoacetamide and sodium methoxide provides 1,2-dihydro-5-(4-fluorophenyl)-2-oxo-3-pyridinecarbonitrile. Hydrolysis of this product with acid gives 1,2-dihydro-5-(4-fluorophenyl)-2-oxo-3-pyridinecarboxylic acid. Treatment of this product with quinoline affords 5-(4-fluorophenyl)-2(1H)-pyridone, which is reacted with phosphorus oxychloride to give 2-chloro-5-(4-fluorophenyl)pyridine. Treatment of the above product with hydrazine produces 2-hydrazino-5-(4-fluorophenyl)pyridine. Treatment of this product with ethyl orthoacetate produces 6-(4-fluorophenyl)-3-methyl-1,2,4-triazolor[4,3-a]pyridine which yields the product of the Example on hydrogenation.
Sources & evidence
- ORD record
- ord-f055b93bedb34b7eb0e05f6d5e8ad18e
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04244953
Reaction notes
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