Hydrochloric Acid → 1-[4-(1-Imidazolyl)-phenyl]-2-propanone

HRID 364937Notes

Reaction equation

HRID 364937 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]=[C:13]([N+]([O-])=O)[CH3:14])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.C[OH:20]>O.[Fe]>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13](=[O:20])[CH3:14])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 540019184-(2-nitro-1-propenyl)phenyl-1H-imidazole

Product 1

HCID 133942271-[4-(1-Imidazolyl)-phenyl]-2-propanone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-[4-(1H-imidazol-1-yl)phenyl]-2-nitropropene prepared above, iron powder (94.7 grams), and hydrated iron (III) chloride (1.2 grams) in 50 ml of methanol and 170 ml of water is heated to reflux and treated dropwise with 85 ml of 12 N hydrochloric acid over four hours. After heating under reflux for one additional hour, the reaction mixture is cooled, and filtered. The filtrate is made basic with 40% ammonium hydroxide solution and the entire mixture is extracted thoroughly with ethyl acetate. The ethyl acetate is treated with charcoal, dried (magnesium sulfate) and concentrated on the rotary evaporator to give a dark yellow oil. This material is chromatographed on a Waters Prep 500A, using silica gel and eluting with 2% methanol in chloroform. The main fraction contains 1-[-4-(1H-imidazol-1-yl)-phenyl]-2-propanone.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. temperatureAfter heating
  4. temperatureunder reflux for one additional hour
  5. temperaturethe reaction mixture is cooled
  6. filtrationfiltered
  7. extractionthe entire mixture is extracted thoroughly with ethyl acetate
  8. additionThe ethyl acetate is treated with charcoal
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated on the rotary evaporator
  11. customto give a dark yellow oil
  12. customThis material is chromatographed on a Waters Prep 500A
  13. washeluting with 2% methanol in chloroform

Sources & evidence

ORD record
ord-1dc8c74636294ac8848c6a73cb3798de
Source dataset
uspto-grants-1986_08
Patent number
US04607037

Reaction notes

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