Ethanolamine → 1,2-Dimethyl-4-phenyl-1H-pyrrole

HRID 880437Notes

Reaction equation

HRID 880437 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5](C(O)=O)[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:3]1C(O)=O.NCCO>O>[CH3:1][N:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:5]=[C:6]1[CH3:7]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 669150311,5-dimethyl-3-phenyl-1H-pyrrole-2,4-dicarboxylic acid

Product 1

HCID 447182881,2-Dimethyl-4-phenyl-1H-pyrroleYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

A suspension of 1,5-dimethyl-3-phenyl-pyrrole-2,4-dicarboxylic acid (60 g, 0.23 mol) and 2-aminoethanol (300 mL) was heated to 175° C. under a nitrogen atmosphere for 30 min. The mixture was allowed to cool to room temperature, diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed successively with water (3×100 mL) and brine (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo at a temperature below 40° C. to afford the crude product. Flash column chromatography over neutral alumina using 5% ethyl acetate in petroleum ether as eluent afforded 1,2-dimethyl-4-phenyl-pyrrole (30.5 g, 78%) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers were washed successively with water (3×100 mL) and brine (2×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo at a temperature below 40° C.
  6. customto afford the crude product

Sources & evidence

ORD record
ord-16bfd1830fb840d4b93c119aed111638
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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