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

HRID 1649431Notes

Reaction equation

HRID 1649431 reaction equation
[F:1][C:2]1[C:3]([NH:13][C:14](=[O:16])[CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[H][H]>[Pt].C(O)(=O)C>[F:1][C:2]1[C:3]([NH:13][C:14](=[O:16])[CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH3:12])[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 12896814N-(6-Fluoro-2-methylquinolin-5-yl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 15571780N-(6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-5-yl)acetamideYield 98.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8 g of 6-fluoro-5-acetylamino-quinaldine and 0.2 g of 5% platinum on carbon was dissolved in 80 ml of acetic acid and the solution was subjected to catalytic hydrogenation according to Parr method at a hydrogen pressure of 4 kg/cm2. After a theoretical amount of hydrogen was absorbed the reaction mixture was filtered. The filtrate was then concentrated under reduced pressure to obtain 8 g of 6-fluoro-5-acetylamino-1,2,3,4-tetrahydroquinaldine as an oily product. Production of this compound was confirmed by NMR spectral analysis and mass spectral analysis.

Workup

  1. customAfter a theoretical amount of hydrogen was absorbed the reaction mixture
  2. filtrationwas filtered
  3. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-98eea271b804499fac222a04606cb92e
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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