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

HRID 1995321Notes

Reaction equation

HRID 1995321 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 was dissolved 95 g of 5-acetamido-6-fluoroquinaldine. To this mixture was added 10 g of five percent platinum on charcoal. The mixture was hydrogenated with hydrogen gas at 30 psi on a Parr 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-b0804705673d4d5ea3783d3003485c71
Source dataset
uspto-grants-1983_09
Patent number
US04404207

Reaction notes

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