Methyl vinyl ketone → HCID 68577397, compound

HRID 640686Notes

Reaction equation

HRID 640686 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[CH:11]([C:13]([CH3:15])=O)=[CH2:12]>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:6]2[C:5]=1[C:13]([CH3:15])=[CH:11][CH:12]=[N:7]2)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 74233-Nitroaniline

Product 1

HCID 68577397HCID 68577397, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3-nitroaniline (1 g. 7.2 mmol.) in acetic acid (10 ml), activated silferc (1.15 g. ferric chloride 7.2 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and methyl vinyl ketone (MVK) (0.55 g, 7.9 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 (1.0 g. 7.2 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 64%.

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-75acf43457b24ff3a4d84dccf7537063
Source dataset
uspto-grants-2010_04
Patent number
US07692016B2

Reaction notes

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