Pyridine → 1-(2-Acetylaminoethyl)-2,5-dimethylpyrrole-3-carbonitrile

HRID 1089431Notes

Reaction equation

HRID 1089431 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][N:7]1[C:11]([CH3:12])=[CH:10][C:9]([CH:13]=O)=[C:8]1[CH3:15])(=[O:3])[CH3:2].Cl.NO.[N:19]1C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([NH:4][CH2:5][CH2:6][N:7]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]#[N:19])=[C:8]1[CH3:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 178134N-(2-(3-Formyl-2,5-dimethyl-1H-pyrrol-1-yl)ethyl)acetamideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 145367451-(2-Acetylaminoethyl)-2,5-dimethylpyrrole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.2 g (0.025 mol) of 1-(2-acetylaminoethyl)-2,5-dimethylpyrrole-3-aldehyde, 1.75 g (0.025 mol) of hydroxylamine hydrochloride and 2 ml (0.025 mol) of pyridine are heated under reflux in 25 ml of toluene for 1.5 hours. After the mixture has been concentrated, the residue is taken up in water, the mixture is extracted with methylene chloride and the product is recrystallized from toluene.

Workup

  1. concentrationAfter the mixture has been concentrated
  2. extractionthe mixture is extracted with methylene chloride
  3. customthe product is recrystallized from toluene

Sources & evidence

ORD record
ord-418c1f690c9444beb44ce2e475a5d1a4
Source dataset
uspto-grants-1990_10
Patent number
US04966901

Reaction notes

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