HCID 57756898, compound → HCID 57756924, compound

HRID 227685Notes

Reaction equation

HRID 227685 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[CH:13][NH:12][C:11]=2[C:15]([NH2:17])=[O:16])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]=[CH:13][NH:12][C:11]=2[C:15]([NH2:17])=[O:16])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 57756898HCID 57756898, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57756924HCID 57756924, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 0.009 g (0.081 mmol) of 10% palladium-on-charcoal in 20 cm3 of methanol is added, at a temperature in the region of 20° C., 0.04 g (0.172 mmol) of 5-(4-nitrophenyl)-3H-imidazole-4-carboxamide. After hydrogenating for 3 hours in an autoclave under 3 bar of hydrogen, at a temperature in the region of 25° C., the reaction mixture is filtered. The catalyst is rinsed with twice 2 cm3 of methanol and the filtrate is then concentrated to dryness under reduced pressure (2.7 kPa) to give 0.034 g of 5-(4-aminophenyl)-3H-imidazole-4-carboxamide in the form of a brown solid; EI: m/z=202: M+; Cl: m/z=203: [M+H]+; ES+: m/z=203: [M+H]+; ES−: m/z=201: [M−H]−.

Workup

  1. filtrationthe reaction mixture is filtered
  2. washThe catalyst is rinsed with twice 2 cm3 of methanol
  3. concentrationthe filtrate is then concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-83d09d3972274214b2a267dcfb446759
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Reaction notes

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