Nitric Acid → 2,2,2-Trichloro-1-(1-methyl-4-nitro-1H-pyrrol-2-yl)ethan-1-one

HRID 1857069Notes

Reaction equation

HRID 1857069 reaction equation
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[N+:12]([O-:15])(O)=[O:13].[CH:16](O)(C)C>C(OC(=O)C)(=O)C>[N+:12]([C:8]1[CH:9]=[C:5]([C:3](=[O:4])[C:2]([Cl:1])([Cl:10])[Cl:11])[N:6]([CH3:16])[CH:7]=1)([O-:15])=[O:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3776IsopropanolHCID 3214872-(Trichloroacetyl)pyrrole

Product 1

HCID 27599662,2,2-Trichloro-1-(1-methyl-4-nitro-1H-pyrrol-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
-40 °C

Procedure

To a well stirred solution of trichloroacetyl chloride (1 kg, 5.5 mole) in 1.5 liter ethyl ether in a 12 liter flask was added dropwise over a period of 3 h a solution of N-methylpyrrole (0.45 kg, 5.5 mole) in 1.5 liter anhydrous ethyl ether. The reaction was stirred for an additional 3 hours and quenched by the dropwise addition of a solution of 400 g potassium carbonate in 1.5 liters water. The layers were separated and the ether layer concentrated in vacuo to provide 2-(trichloroacetyl)pyrrole (1.2 kg, 5.1 mol) as a yellow crystalline solid sufficiently pure to be used without further purification. To a cooled (-40° C.) solution of 2-(trichloroacetyl) pyrrole (1.2 kg, 5.1 mol) in acetic anhydride (6 L) in a 12 L flask equipped with a mechanical stirrer was added 440 mL fuming nitric acid over a period of 1 hour while maintaining a temperature of (-40° C.). The reaction was carefully allowed to warm to room temperature and stir an additional 4 h. The mixture was cooled to -30° C., and isopropyl alcohol (6 L) added. The solution was stirred at -20° C. for 30 min during which time a white precipitate forms. The solution was allowed to stand for 15 min and the resulting precipitate collected by vacuum filtration.

Workup

  1. customto be used without further purification
  2. customequipped with a mechanical stirrer
  3. additionwas added 440 mL
  4. customof 1 hour
  5. temperatureto warm to room temperature
  6. temperatureThe mixture was cooled to -30° C.
  7. stirringThe solution was stirred at -20° C. for 30 min during which time a white precipitate forms
  8. waitto stand for 15 min
  9. filtrationthe resulting precipitate collected by vacuum filtration

Sources & evidence

ORD record
ord-bca575d7b6e442a983ae18b4c550dbb3
Source dataset
uspto-grants-2000_11
Patent number
US06143901

Reaction notes

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