Water → 3-(4-Nitrophenyl)pyrrole

HRID 222570Notes

Reaction equation

HRID 222570 reaction equation
C(OC([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:9][NH:8][CH:7]=1)=O)C.[OH-].[Na+].O.C(Cl)Cl>C(O)CO>[N+:17]([C:14]1[CH:13]=[CH:12][C:11]([C:10]2[CH:6]=[CH:7][NH:8][CH:9]=2)=[CH:16][CH:15]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 53440113ethyl 4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 214134213-(4-Nitrophenyl)pyrroleYield 26.9%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

A solution of 55 (2.44 g, 9.92 mmol) in ethylene glycol (25 mL) was flushed with argon for 20 min. The mixture was immersed in an oil bath pre-heated to 160° C., and powdered NaOH (4.22 g, 105 mmol) was added. Stirring was continued for 1.5 h. The reaction mixture was allowed to cool to room temperature, and water and CH2Cl2 were added. The aqueous layer was extracted with CH2Cl2. The organic extract was washed with water and brine. The organic layer was dried (Na2SO4). The solvent was removed at reduced pressure to yield a pale brown oil (502 mg, 25%): 1H NMR δ 6.36-6.48 (m, 1H), 6.69-6.73 (m, 2H), 6.79-6.81 (m, 1H), 6.96-6.98 (m, 1H), 7.33-7.38 (m, 1H), 8.21 (br, 1H).

Workup

  1. customThe mixture was immersed in an oil bath
  2. temperatureto cool to room temperature
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-7524f10eecfe4d8ab85352ab422caf04
Source dataset
uspto-grants-2012_06
Patent number
US08207329B2

Reaction notes

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