p-Toluenesulfonic acid → 1-(3-nitrophenyl)-1H-pyrrole

HRID 581932Notes

Reaction equation

HRID 581932 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[CH:13]=[CH:17][CH:16]=[CH:15]2)[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74233-NitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 2724341-(3-nitrophenyl)-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-nitroaniline (15 g, 0.11 mmol), 2,5-dimethoxytetrahydrofuran (42 ml, 0.33 mol) and a catalytic amount of pTSA in dry toluene (150 ml) is heated to reflux for 2 hours. After cooling the mixture is concentrated under reduced pressure and the residue is purified by column-chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (1:1) as the eluent. Yield: 16 g (78%). Mp 65-70° C.

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureAfter cooling the mixture
  3. concentrationis concentrated under reduced pressure
  4. customthe residue is purified by column-chromatography on silica gel using
  5. additiona mixture of ethyl acetate and petroleum ether (1:1) as the eluent

Sources & evidence

ORD record
ord-fad5bf03b4244b9c9fba04096ba9e90f
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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