4-Isopropylaniline → HCID 4105194, compound

HRID 2270582Notes

Reaction equation

HRID 2270582 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1>C(O)(=O)C>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH:13]=[CH:17][CH:16]=[CH:15]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 74644-IsopropylanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 4105194HCID 4105194, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Glacial acetic acid (100 ml) was added to a mixture of 4-isopropylaniline (10 ml, 72.4 mmol) and 2,5-dimethoxytetrahydrofuran (9.6 ml, 72.4 mmol) and the resulting mixture was refluxed for 1.5 h. The reaction mixture was allowed to cool and acetic acid was removed under reduced pressure. The resulting brown syrup was dissolved in ethyl acetate (200 ml) and washed with water (2×200 ml). The organic layer was dried over magnesium sulfate and filtered. Removal of the solvent gave 1-(4′-isopropylphenyl)pyrrole (13.28 g, 99% yield) as a brown syrup.

Workup

  1. temperaturethe resulting mixture was refluxed for 1.5 h
  2. temperatureto cool
  3. customacetic acid was removed under reduced pressure
  4. dissolutionThe resulting brown syrup was dissolved in ethyl acetate (200 ml)
  5. washwashed with water (2×200 ml)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-8a6923fa8f4b4a27bd43b986c215cc25
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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