Acetic Anhydride → 1-Acetyl-3-cyano-4-phenylpyrrole

HRID 903903Notes

Reaction equation

HRID 903903 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][NH:5][CH:4]=1)#[N:2].[C:14](OC(=O)C)(=[O:16])[CH3:15]>O>[C:14]([N:5]1[CH:6]=[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:3]([C:1]#[N:2])=[CH:4]1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 37214604-Phenyl-1H-pyrrole-3-carbonitrile

Product 1

HCID 233355631-Acetyl-3-cyano-4-phenylpyrrole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 g of 3-cyano-4-phenylpyrrole (Compound No. 8) was added to 20 ml of acetic anhydride and heated for 4 hours in oil-bath of 140°-150° C. After cooling, the resulting reaction mixture was poured into about ten-times volume of cold water to decompose excess acetic anhydride. The resulting precipitate was filtrated, washed with water and dried to obtain 4.5 g of crystal. The crystal was recrystallized from methyl alcohol to obtain 3 g of the desired product.

Workup

  1. temperatureheated for 4 hours in oil-bath of 140°-150° C
  2. temperatureAfter cooling
  3. customthe resulting reaction mixture
  4. filtrationThe resulting precipitate was filtrated
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-14e7ac18f05e4d2fa6efee89e661e553
Source dataset
uspto-grants-1980_10
Patent number
US04229465

Reaction notes

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