Acetic Anhydride → N-Acetyloxymethyl-3-(2-chlorophenyl)-4-cyanopyrrole

HRID 1285300Notes

Reaction equation

HRID 1285300 reaction equation
[OH:1][CH2:2][N:3]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[CH:4]1.CN(C1C=CC=CN=1)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1>[C:26]([O:1][CH2:2][N:3]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[CH:4]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 202487964-(2-Chlorophenyl)-1-(hydroxymethyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 20248792N-Acetyloxymethyl-3-(2-chlorophenyl)-4-cyanopyrrole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

41.4 g of N-hydroxymethyl-3-(2-chlorophenyl)-4-cyanopyrrole are dissolved in 350 ml of pyridine and 1.8 g of dimethylaminopyridine are added. Then 21.4 ml of acetic anhydride are slowly added dropwise at 0° to 7° C. and the mixture is stirred for 12 hours. The reaction mixture is then poured into ice-water and extracted twice with ethyl acetate. The extracts are washed twice with dilute ice-cold hydrochloric acid and twice with a semi-saturated aqueous solution of sodium chloride, dried over sodium sulfate and filtered. The filtrate is concentrated and the residue is recrystallised from diethyl ether/hexane to give the title compound in the form of colourless crystals with a melting point of 91°-95° C.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe extracts are washed twice with dilute ice-cold hydrochloric acid and twice with a semi-saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is recrystallised from diethyl ether/hexane

Sources & evidence

ORD record
ord-f9766cd5b99d4315ad838694b097756a
Source dataset
uspto-grants-1986_01
Patent number
US04567052

Reaction notes

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