Water → 1-(3,5-Dinitrophenyl)pyrrole

HRID 896238Notes

Reaction equation

HRID 896238 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH2:7])([O-:3])=[O:2].CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1.O>CC(O)=O>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[CH:16]=[CH:20][CH:19]=[CH:18]2)[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 120683,5-DinitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 173821411-(3,5-Dinitrophenyl)pyrrole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

According to Scheme 16, a solution of 3,5-dinitroaniline (1.83 g, 10 mmol) and 2,5-dimethoxytetrahydrofuran in 20 mL of HOAc was refluxed overnight. The reaction mixture was poured into water and extracted with EtOAc. The ethyl acetate layer was washed with water followed by aq NaHCO3 and brine. After drying, the solvent was removed to provide 1.52 g of 1-(3,5-dinitrophenyl)pyrrole.

Workup

  1. extractionextracted with EtOAc
  2. washThe ethyl acetate layer was washed with water
  3. customAfter drying
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-f07cc72beff84db4abc6771b29cf13bd
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

Loading…