Methyl 1-methyl-5-nitro-1H-pyrrole-2-carboxylate → Methyl 5-amino-1-methyl-1H-pyrrole-2-carboxylate

HRID 726477Notes

Reaction equation

HRID 726477 reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-])=O)=[CH:5][CH:4]=[C:3]1[C:10]([O:12][CH3:13])=[O:11]>[Pd].CO>[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]1[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 1

HCID 14487173Methyl 1-methyl-5-nitro-1H-pyrrole-2-carboxylate

Product 1

HCID 16085054Methyl 5-amino-1-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.31 g (7.4 mmol) of methyl N-methyl-5-nitro-2-pyrrolecarboxylate, 400 mg of palladium on carbon (10%) and 50 ml of methanol were introduced into a reactor. The mixture was hydrogenated at room temperature and at a pressure of 7 bar for 2 hours. The catalyst was filtered, washed twice with 25 ml of methanol and the filtrates evaporated. 1.1 g (100%) of the expected amine was recovered in the form of a dark red oil.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed twice with 25 ml of methanol
  3. customthe filtrates evaporated
  4. custom1.1 g (100%) of the expected amine was recovered in the form of a dark red oil

Sources & evidence

ORD record
ord-240b193a74654233bc58222f2f2de360
Source dataset
uspto-grants-1998_01
Patent number
US05709867

Reaction notes

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