ethyl 4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate → ethyl 4-(4-aminophenyl)-1H-pyrrole-3-carboxylate

HRID 734628Notes

Reaction equation

HRID 734628 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][NH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CO.C(OCC)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][NH:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 53440113ethyl 4-(4-nitrophenyl)-1H-pyrrole-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 69064082ethyl 4-(4-aminophenyl)-1H-pyrrole-3-carboxylateYield 44.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.2 g (0.769 mmol) of ethyl 4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate is added at a temperature in the region of 20° C. to a suspension of 0.02 g (0.188 mmol) of 10% palladium on carbon in 15 cm3 of methanol. After hydrogenating for 20 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 three times 5 cm3 of methanol and then the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is stirred in 10 cm3 of diethyl ether and then filtered and dried under reduced pressure (2.7 kPa) to give 0.079 g of ethyl 4-(4-aminophenyl)-1H-pyrrole-3-carboxylate, in the form of a brown solid; EI: m/z=230 (M+) base peak, m/z=202 (M-C2H4+), m/z=157 (M-C2H5O+).

Workup

  1. filtrationthe 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)
  4. customto give a residue which
  5. filtrationfiltered
  6. customdried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-4910756467224a459cb9a3536399b6cd
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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