Water → 1-(4-Ethoxy-2-nitrophenyl)-2,5-dimethyl-1H-pyrrole

HRID 2375423Notes

Reaction equation

HRID 2375423 reaction equation
[CH2:1]([CH2:5][C:6](=O)[CH3:7])[C:2]([CH3:4])=O.[CH2:9]([O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1)[CH3:10].O>C(O)(=O)C>[CH3:7][C:6]1[N:16]([C:15]2[CH:17]=[CH:18][C:12]([O:11][CH2:9][CH3:10])=[CH:13][C:14]=2[N+:19]([O-:21])=[O:20])[C:2]([CH3:4])=[CH:1][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80352,5-HexanedioneHCID 692294-Ethoxy-2-nitroaniline

Product 1

HCID 692756781-(4-Ethoxy-2-nitrophenyl)-2,5-dimethyl-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of acetonyl acetone (1.95 mL, 16.5 mmol) in acetic acid (100 mL) was added 4-ethoxy-2-nitroaniline (3.0 g, 16.5 mmol) and the red mixture heated at reflux overnight. After cooling to rt, the now black solution was poured into water and extracted with EtOAc (2×200mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to an oil. Purification by flash chromatography (10% EtOAc/hexanes) gave 2,5-dimethyl-1-(4-ethoxy-2-nitrophenyl)pyrrole as a red oil: 1H NMR (CDCl3, 500 MHz) δ 7.46 (d, 1H), 7.27 (t, 1H), 7.19 (dd, 1H), 5.91 (s, 2H), 4.15 (q, 1H), 1.96 (s, 6H), 1.50 (t, 3H); MS (ESI) 261 (M+H)+.

Workup

  1. temperaturethe red mixture heated
  2. temperatureat reflux overnight
  3. extractionextracted with EtOAc (2×200mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to an oil
  8. customPurification by flash chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-066fb788756e47be8beeffd05cfe04c4
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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