4-Nitrobenzoic Acid → Benzoic acid, 4-nitro-, hydrazide
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][NH2:14]>>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:13][NH2:14])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
Procedure
4-Nitro benzoic acid can be reacted with hydrazine to give 4-nitrobenzoic acid hydrazide. This acid hydrazide can be reacted with 2,4-dichlorobenzaldehyde to yield the corresponding acid hydrazone adduct of 2,6-dichlorobenzoldehyde. Treatment of this material with acetic anhydride according to the method of J. Chem. Research Synopsis, 1995, 88-89 can lead to the corresponding N-acetylated 4,5-dihydrooxadiazole. Basic hydrolysis can yield the N-deacetylated product which can be reduced with tin dichloride or with iron powder and ammonium chloride to yield the corresponding aniline. This racemic aniline can be treated with 2,2-dichloroacetyl chloride and triethylamine to yield (±)-2,2-dichloro-N-[4-[5-(2,6-dichlorophenyl)-2-(4,5-dihydrooxadiazolyl)phenyl]acetamide.
Sources & evidence
- ORD record
- ord-fff5ef77f96f4ee49f2f90f688cbb678
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326790B2
Reaction notes
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