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

HRID 981588Notes

Reaction equation

HRID 981588 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-phenyl-hexane-1,4-dione (Example 2) and 9.3 mmol (102 mmol) of aniline in 150 ml of toluene are heated under reflux in a water separator for 24 hours with the addition of 500 mg of p-toluenesulphonic acid. After cooling and diluting with ethyl acetate, the reaction mixture is washed with 1 N hydrochloric acid and then with sodium bicarbonate solution, dried over magnesium sulphate and concentrated in vacuo. The residue is then chromatographed on silica gel.

Workup

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

Sources & evidence

ORD record
ord-17b23d844ecc492c8f3c954c774dbf54
Source dataset
uspto-grants-1991_02
Patent number
US04992462

Reaction notes

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