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

HRID 1995318Notes

Reaction equation

HRID 1995318 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 compound 5-acetamido-6-fluoroquinaldine. This intermediate is further reduced catalytically in the presence of platinum on charcoal to provide the compound 5-acetamido-6-fluorotetrahydroquinaldine.

Sources & evidence

ORD record
ord-c484abe74ac74ccdaf6743385c9d9384
Source dataset
uspto-grants-1983_09
Patent number
US04404207

Reaction notes

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