Aniline → 4-Methylquinoline

HRID 640677Notes

Reaction equation

HRID 640677 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([C:10]([CH3:12])=O)=[CH2:9]>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:12][C:10]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:1]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 6570Methyl vinyl ketone

Product 1

HCID 102854-MethylquinolineYield 55%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of aniline (1 g. 10 mmol) in acetic acid (10 ml), activated silferc (1.72 g. ferric chloride 10 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and methyl vinyl ketone (MVK) (0.83 g, 11.8 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 (1.46 g. 10 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 55%.

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-dc6f2d9342644a2daa4b932a0d12803d
Source dataset
uspto-grants-2010_04
Patent number
US07692016B2

Reaction notes

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