Methyl vinyl ketone → 4,6-Dimethylquinoline

HRID 640681Notes

Reaction equation

HRID 640681 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]([C:11]([CH3:13])=O)=[CH2:10]>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:13][C:11]1[C:7]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:8]=2)[N:6]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 7813p-Toluidine

Product 1

HCID 700054,6-DimethylquinolineYield 60%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 4-methylaniline (1 g. 9.3 mmol.) in acetic acid (10 ml), activated silferc (1.5 g. ferric chloride 9.3 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and methyl vinyl ketone (MVK) (0.72 g, 10 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 (1.27 g. 9.3 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 60%.

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-a0c31c3abfec4e28a6f630f4ad006404
Source dataset
uspto-grants-2010_04
Patent number
US07692016B2

Reaction notes

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