HCID 14500642, compound → HCID 14500643, compound

HRID 1761592Notes

Reaction equation

HRID 1761592 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10](=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=1)[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10](=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 14500642HCID 14500642, compound

Product 1

HCID 14500643HCID 14500643, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 19 g (80 mmol) of 1-butyl-2-(3'-nitrobenzoyl)pyrrole in 250 ml of methanol was hydrogenated at 45 p.s.i. in the presence of 3 g of a 10% palladium-charcoal catalyst. After 45 minutes the catalyst was separated by filtration and the filtrate evaporated under reduced pressure. Purification of the residue by column chromatography on 750 g of silica gel, using hexane-ethyl acetate (75:25) as eluant, afforded 16.6 g (95%) of 1-butyl-2-(3'-aminobenzoyl)pyrrole, the title compound, as an oil.

Workup

  1. customAfter 45 minutes the catalyst was separated by filtration
  2. customthe filtrate evaporated under reduced pressure
  3. customPurification of the residue by column chromatography on 750 g of silica gel

Sources & evidence

ORD record
ord-ddd8729e2a8e46ca95f608e39ea2ad42
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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