Water → HCID 22493292, compound

HRID 1816294Notes

Reaction equation

HRID 1816294 reaction equation
[CH2:1]([CH2:5][C:6](=O)[CH3:7])[C:2]([CH3:4])=O.[N+:9]([C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14])([O-:11])=[O:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:4][C:2]1[N:14]([C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[N+:9]([O-:11])=[O:10])[C:6]([CH3:7])=[CH:5][CH:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 69462-NitroanilineHCID 80352,5-HexanedioneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 22493292HCID 22493292, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetonylacetone (2.0 g, 17.5 mmol), o-nitroaniline (2.6 g, 18.8 mmol, 1.07 eq), and p-toluenesulfonic acid monohydrate (0.31 g, 1.63 mmol) in toluene (75 mL) were heated at reflux with azeotropic removal of water overnight. The crude product was purified by column chromatography over silica gel to give 2.28 g of 2,5-dimethyl-1-(2-nitrophenyl)-1H-pyrrole, which was reduced as in Example 64 to give 0.46 g of 2-(2,5-dimethyl-1H-pyrrol-1-yl)benzenamine.

Workup

  1. customThe crude product was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-de765f63a5134e54a6d2a1122d58a495
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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