4-Isopropylaniline → HCID 4105194, compound

HRID 232743Notes

Reaction equation

HRID 232743 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-5a992e8196a44195b5410bfb613272c6
Source dataset
uspto-grants-1997_01
Patent number
US05591761

Reaction notes

Loading…