HCID 14500623, compound → HCID 14500624, compound

HRID 1761581Notes

Reaction equation

HRID 1761581 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][CH3:11])=[CH:8][CH:7]=[C:6]1[C:12](=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=1)[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([N:5]1[C:9]([CH2:10][CH3:11])=[CH:8][CH:7]=[C:6]1[C:12](=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 14500623HCID 14500623, compound

Product 1

HCID 14500624HCID 14500624, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 11.9 g (39 mmol) of 1-butyl-2-(3'-nitrobenzoyl)-5-ethylpyrrole in 100 ml of methanol was hydrogenated at 45 p.s.i. in the presence of 3 g of 10% palladium-charcoal catalyst for 1 hour. The catalyst was then separated by fltration and the filtrate evaporated under reduced pressure. The residue was purified by column chromatography on 500 g of silica gel, using hexane-acetone (95:5) as eluant, to produce 6.5 g (60%) of 1-butyl-2-(3'-aminobenzoyl)-5-ethylpyrrole, the pure title compound, which was recrystallized from hexane. M.P. 71°-7° C.

Workup

  1. customThe catalyst was then separated by fltration
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on 500 g of silica gel

Sources & evidence

ORD record
ord-860f8c85f095405b89e3a655bf7206a2
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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