Methyl vinyl ketone → 8-Fluoro-4-methylquinoline

HRID 640684Notes

Reaction equation

HRID 640684 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:9]([C:11]([CH3:13])=O)=[CH2:10]>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[CH:10][CH:9]=[C:11]2[CH3:13]

Participants

5

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 95842-Fluoroaniline

Product 1

HCID 167342108-Fluoro-4-methylquinolineYield 65%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-fluoroaniline (1 g. 9.0 mmol.) in acetic acid (10 ml), activated silferc (1.4 g. ferric chloride 9.0 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and methyl vinyl ketone (MVK) (0.7 g, 9.9 mmol) was added slowly over a period of 15 minutes. The reaction mixture was heated to 70° C. and maintained between 70-75° C. for one hour. Anhydrous zinc chloride (1.2 g. 9.0 mmol) was added and the reaction was further refluxed for two hours. The reaction mixture was cooled, filtered, basified with 10% NaOH solution, extracted with ethyl acetate (3×20 ml), dried over Na2SO4 and evaporated to give the product; Yield 65%.

Workup

  1. temperaturemaintained between 70-75° C. for one hour
  2. temperaturethe reaction was further refluxed for two hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. extractionextracted with ethyl acetate (3×20 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto give the product

Sources & evidence

ORD record
ord-18e52ef55dc5442086277e00cee3b959
Source dataset
uspto-grants-2010_04
Patent number
US07692016B2

Reaction notes

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