Acetic Anhydride → N-(6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-5-yl)acetamide
Reaction equation
C(OC(=O)C)(=O)C.[C:8]([NH:11][C:12]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([CH3:23])=[N:17]2)(=[O:10])[CH3:9]>[Pd].[Pt]>[C:8]([NH:11][C:12]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]2[C:13]=1[CH2:14][CH2:15][CH:16]([CH3:23])[NH:17]2)(=[O:10])[CH3:9]Participants
5
Procedure
The nitro group is reduced catalytically, for example in the presence of palladium on charcoal. If this reaction is carried out in the presence of acetic anhydride the product is the novel compound 5-acetamido-6-fluoroquinaldine. This intermediate is further reduced catalytically in the presence of platinum on charcoal to provide the novel compound 5-acetamido-6-fluorotetrahydroquinaldine.
Sources & evidence
- ORD record
- ord-7b11ab5103034da5a729144a9f541223
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04691016
Reaction notes
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