Methyl vinyl ketone → 8-Methoxy-4-methylquinoline

HRID 640678Notes

Reaction equation

HRID 640678 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[CH:10]([C:12]([CH3:14])=O)=[CH2:11]>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:4]=1[N:5]=[CH:11][CH:10]=[C:12]2[CH3:14]

Participants

5

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 70002-Methoxyaniline

Product 1

HCID 154374508-Methoxy-4-methylquinolineYield 60%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-methoxyaniline (1 g. 8.1 mmol.) in acetic acid (10 ml), activated silferc (1.3 g. ferric chloride 8.1 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and methyl vinyl ketone (MVK) (0.62 g, 8.9 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 (1.1 g. 8.1 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-81270b95bc934078a58d8da65b70befb
Source dataset
uspto-grants-2010_04
Patent number
US07692016B2

Reaction notes

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