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

HRID 2308809Notes

Reaction equation

HRID 2308809 reaction equation
[C:1]([NH:4][C:5]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([CH3:16])=[N:10]2)(=[O:3])[CH3:2].[H][H]>C(O)(=O)C.[Pt]>[C:1]([NH:4][C:5]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH:9]([CH3:16])[NH:10]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 12896814N-(6-Fluoro-2-methylquinolin-5-yl)acetamideHCID 178418361HCID 178418361, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

In one liter of acetic acid were dissolved 95 g of 5-acetamido-6-fluoroquinaldine. To this mixture were added 10 g of five percent platinum on charcoal. The mixture was hydrogenated with hydrogen gas at 30 psi on a Paar apparatus for five hours. The amount of hydrogen used was 61 psi (versus 62 psi theoretical). The catalyst was removed by filtration, the filtrate was concentrated to 250 ml and decanted into cold stirred sodium hydroxide solution. The white precipitate was separated by filtration and triturated with a chloroform/hexane (50/50) mixture to provide white crystals of 5-acetamido-6-fluorotetrahydroquinaldine, m.p. 168°-170° C. The structural assignment was confirmed by infrared spectral analysis.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to 250 ml
  3. customdecanted
  4. customThe white precipitate was separated by filtration
  5. customtriturated with a chloroform/hexane (50/50) mixture

Sources & evidence

ORD record
ord-944d359fedc0426397fc855d354a532b
Source dataset
uspto-grants-1987_09
Patent number
US04691016

Reaction notes

Loading…