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

HRID 435114Notes

Reaction equation

HRID 435114 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-0226b0fe0fa6485ca63ce9bb393a4eb1
Source dataset
uspto-grants-1983_08
Patent number
US04400386

Reaction notes

Loading…