Sulfuric Acid → 1-(2-Acetylaminoethyl)-2,5-dimethyl-3-nitropyrrole

HRID 1089434Notes

Reaction equation

HRID 1089434 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][N:7]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]1[CH3:13])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[N+:19]([O-])([O-:21])=[O:20].[K+]>>[C:1]([NH:4][CH2:5][CH2:6][N:7]1[C:8]([CH3:13])=[CH:9][C:10]([N+:19]([O-:21])=[O:20])=[C:11]1[CH3:12])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 13770049N-(2-(2,5-Dimethyl-1H-pyrrol-1-yl)ethyl)acetamide

Product 1

HCID 145367501-(2-Acetylaminoethyl)-2,5-dimethyl-3-nitropyrrole

Procedure

18.0 g (0.1 mol) of 1-(2-acetylaminoethyl)-2,5-dimethylpyrrole are introduced into 54 ml of concentrated sulphuric acid at -10° C., during which the temperature rises to 9° C. After the mixture has been subsequently stirred for 5 minutes, 10.9 g (0.11 mol) of potassium nitrate are introduced at about 5° C. After further stirring for 30 minutes, the mixture is poured onto 300 g of ice and extracted with methylene chloride, the extract is concentrated and the residue is chromatographed over a short silica gel column.

Workup

  1. customrises to 9° C
  2. stirringAfter further stirring for 30 minutes
  3. extractionextracted with methylene chloride
  4. concentrationthe extract is concentrated
  5. customthe residue is chromatographed over a short silica gel column

Sources & evidence

ORD record
ord-d44c4ab4232d42978db993802cfe071a
Source dataset
uspto-grants-1990_10
Patent number
US04966901

Reaction notes

Loading…