HCID 86621475, compound → HCID 86621474, compound

HRID 734632Notes

Reaction equation

HRID 734632 reaction equation
[CH:1]([NH:3][C:4]1[NH:5][CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[C:8]=1[C:9]([NH2:11])=[O:10])=[O:2].[H][H]>[Pd].CO>[CH:1]([NH:3][C:4]1[NH:5][CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[C:8]=1[C:9]([NH2:11])=[O:10])=[O:2]

Participants

5

Reactant 2

HCID 86621475HCID 86621475, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86621474HCID 86621474, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.23 g (0.834 mmol) of 2-formylamino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide is added at a temperature in the region of 25° C. to a suspension of 0.030 g (0.0285 mmol) of 10% palladium on carbon in 15 cm3 of methanol. After hydrogenation for 5 hours in an autoclave under 2 bar of hydrogen, at a temperature in the region of 25° C., the reaction mixture is filtered, the catalyst is rinsed with three times 5 cm3 of methanol and then the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give 0.125 g of 2-formylamino-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide, in the form of a green solid. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 5.13 (broad s, 2H); 5.43 (broad m, 1H); 6.27 (d, J=2.5 Hz, 1H); 6.60 (d, J=9.0 Hz, 2H); 6.80 (broad m, 1H); 6.99 (d, J=9.0 Hz, 2H); 8.34 (d, J=1.5 Hz, 1H); 10.9 (broad s, 1H); 11.25 (broad s, 1H)

Workup

  1. filtrationat a temperature in the region of 25° C., the reaction mixture is filtered
  2. washthe catalyst is rinsed with three times 5 cm3 of methanol
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-6d378c9517c5448ba068c7eb8cf7061e
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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