Sodium Hydroxide → 3-fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline

HRID 618316Notes

Reaction equation

HRID 618316 reaction equation
[C:1]([C:9]1[N:13]([CH3:14])[C:12]([CH:15]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=2[F:28])C(OCC)=O)=[CH:11][C:10]=1[CH3:29])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[F:28][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][C:21]=1[CH2:15][C:12]1[N:13]([CH3:14])[C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH3:29])[CH:11]=1)[NH2:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15870184Ethyl 2-(5-benzoyl-1,4-dimethylpyrrol-2-yl)-2-(2-fluoro-4-aminophenyl)acetate

Product 1

HCID 158701853-fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]anilineYield 72.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl 2-(5-benzoyl-1,4-dimethylpyrrol-2-yl)-2-(2-fluoro-4-aminophenyl)acetate (5.3 g, 13.4 mmol) [prepared as in Example 1, Step (c)] and 50% aqueous NaOH (5 ml) were dissolved in a 1:1 mixture of methanol/THF (100 ml), and the reaction mixture was refluxed for 30 min. After removing the solvents in vacuo, the residue was diluted with water and acidified with concentrated HCl. The product was extracted into ethyl acetate, and the organic layer was washed with brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The residue was re-dissolved in DMF (200 ml) and refluxed for 30 min. The reaction mixture was cooled, poured into water/ice, and the product was extracted into ethyl acetate. The organic layer was washed with water and dried over sodium sulfate. Evaporation of the solvent gave 3-fluoro-4-[5-benzoyl-1,4-di-methyl-1H-pyrrol-2-ylmethyl]aniline (3.12 g, 69%) as a solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 30 min
  2. customAfter removing the solvents in vacuo
  3. additionthe residue was diluted with water
  4. extractionThe product was extracted into ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe residue was re-dissolved in DMF (200 ml)
  9. temperaturerefluxed for 30 min
  10. temperatureThe reaction mixture was cooled
  11. additionpoured into water/ice
  12. extractionthe product was extracted into ethyl acetate
  13. washThe organic layer was washed with water
  14. dry with materialdried over sodium sulfate
  15. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4bb20110a8524c45986a2c320cf6fedf
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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