Nitric Acid → 1-(4-Methylphenyl)-4-nitropyrrole-2-carbonitrile

HRID 248365Notes

Reaction equation

HRID 248365 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1.[N+:15]([O-])([OH:17])=[O:16].C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 27977151-(4-Methylphenyl)pyrrole-2-carbonitrile

Product 1

HCID 197594701-(4-Methylphenyl)-4-nitropyrrole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 1-(4-methylphenyl)pyrrole-2-carbonitrile (1.0 g) in acetic anhydride (4 ml) was added nitric acid (231 μl, 94%) dropwise at 5° C. The mixture was stirred at the same temperature for 3 hours and then poured into ice water. The pH was adjusted to 5-7 by the addition of saturated aqueous sodium bicarbonate solution. The separated oil was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, dried, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography to yield 1-(4-methylphenyl)-4-nitropyrrole-2-carbonitrile (471 mg) as a solid.

Workup

  1. extractionThe separated oil was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-69ff63ce454d4085878896b9e6894c5d
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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