3-Nitrobenzamide → 3-Aminobenzamide
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[C:7]([NH:9]C1C(C)=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=1C)=[O:8])([O-])=O.[N+](C1C=C(C=CC=1)C(N)=O)([O-])=O>>[NH2:1][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[C:7]([NH2:9])=[O:8]Participants
Procedure
3-nitro-benzoyl chloride was reacted with an aniline, that is 2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine, to form a 3-nitro-benzamide, that is 3-nitro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide, and c) the 3-nitro-benzamide, that is 3-nitro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide, was reduced to afford the desired 3-amino-benzamide, that is 3-amino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide. Further 3-amino-benzamides were made, for example, by using a substituted 3-nitro-benzoic acid, such as 2-fluoro-3-nitro-benzoic acid, in step a) and/or a different aniline, such as 2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoro-methyl-ethyl)-phenylamine, in step b). Whilst this three step synthesis gives satisfactory results in the laboratory a shorter route to 3-amino-benzamides is required if the carbamate insecticides or bisamide insecticides are to be manufactured on a commercial scale.
Sources & evidence
- ORD record
- ord-af8d5e14fc8541f5bc25c27c963cbb9b
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389767B2
Reaction notes
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