Acetic Anhydride → N-(6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-5-yl)acetamide

HRID 637434Notes

Reaction equation

HRID 637434 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

Reactant 2

HCID 7918Acetic AnhydrideHCID 12896814N-(6-Fluoro-2-methylquinolin-5-yl)acetamide

Product 1

HCID 15571780N-(6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-5-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalyst

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-f870d161d3bd461e9f1bf533a917e00a
Source dataset
uspto-grants-1985_12
Patent number
US04556713

Reaction notes

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