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

HRID 618347Notes

Reaction equation

HRID 618347 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:25])[C:12]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20](Cl)=[CH:19][CH:18]=2)=[C:13]([CH3:15])[CH:14]=1)[NH2:5].C([O-])(=O)C.[Na+]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:25])[C:12]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([CH3:15])[CH:14]=1)[NH2:5]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 538537063-Fluoro-4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline

Product 1

HCID 158701853-fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]anilineYield 55.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Fluoro-4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline (5.0 g, 14.0 mmol), sodium acetate (1.15 g, 14 mmol) and 10% Pd/C (475 mg) were suspended in ethanol (230 ml). The reaction mixture was shaken in a Parr apparatus under hydrogen atmosphere at 30 psi overnight. The mixture was filtered through Celite® and the filtrate was evaporated to dryness. The crude product was purified on a silica gel column (methylene chloride-methanol, 99:1) and then crystallized from ethyl acetate/hexane/cyclohexane to give 3-fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-yl-methyl]aniline (2.49 g, 55%) as a solid.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customthe filtrate was evaporated to dryness
  3. customThe crude product was purified on a silica gel column (methylene chloride-methanol, 99:1)
  4. customcrystallized from ethyl acetate/hexane/cyclohexane

Sources & evidence

ORD record
ord-e0f0124336454619961c1b803e90ce34
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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