Hydrochloric Acid → 4-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}aniline

HRID 618326Notes

Reaction equation

HRID 618326 reaction equation
[CH3:1][C:2]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[O:5].Cl>B#[Ni].CO>[CH3:1][C:2]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 232857664-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene

Product 1

HCID 158701974-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}anilineYield 103.8%

Reagents, catalysts & solvents 2

HCID 82791nickel boride (NiB)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene (0.81 g, 2.3 mmol), [prepared as in Example 7, Step (c)], nickel boride (1.6 g), 1 M HCl (30 ml), and methanol (30 ml) was refluxed for 30 min. The reaction mixture was filtered through a pad of Celite® and the filter cake was washed with ethyl acetate. The filtrate was cooled, made basic with concentrated ammonium hydroxide, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give 4-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}aniline (760 mg, 100%) as an oil.

Workup

  1. temperaturewas refluxed for 30 min
  2. filtrationThe reaction mixture was filtered through a pad of Celite®
  3. washthe filter cake was washed with ethyl acetate
  4. temperatureThe filtrate was cooled
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f3b5f60577ee408482b90dbcd6e78ba3
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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