Water → 3-(4-Fluorophenyl)-5-isopropyl-1,2-diphenylpyrrole

HRID 1086818Notes

Reaction equation

HRID 1086818 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][C:18](=O)[CH:19]([CH3:21])[CH3:20])[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:18]([CH:19]([CH3:21])[CH3:20])[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 143002712-(4-Fluorophenyl)-5-methyl-1-phenylhexane-1,4-dione

Product 1

HCID 144613403-(4-Fluorophenyl)-5-isopropyl-1,2-diphenylpyrrole

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

10.1 g (34 mmol) of 2-(4-fluorophenyl)-5-methyl-1-phenylhexane-1,4-dione (Example 2) and 9.3 g (102 mmol) of aniline are heated under reflux for 24 hours in a water separator in 150 ml of toluene with the addition of 500 mg of p-toluenesulphonic acid. After cooling and diluting with ethyl acetate, the mixture is washed with 1N hydrochloric acid and then with sodium hydrogen carbonate solution, dried over magnesium sulphate and concentrated in vacuo. The residue is then chromatographed over silica gel.

Workup

  1. temperatureAfter cooling
  2. washthe mixture is washed with 1N hydrochloric acid
  3. dry with materialwith sodium hydrogen carbonate solution, dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue is then chromatographed over silica gel

Sources & evidence

ORD record
ord-3d712d5eca9244a8812ebc3d16afb676
Source dataset
uspto-grants-1991_07
Patent number
US05032590

Reaction notes

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