Ethyl Acetate → ethyl 1-(4-aminophenyl)-2-methyl-5-phenylpyrrole-3-carboxylate

HRID 413921Notes

Reaction equation

HRID 413921 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[C:7]=1[CH3:26])=[O:5])[CH3:2].C(OCC)(=O)C>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:17]2[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=2)[C:7]=1[CH3:26])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 2742307HCID 2742307, compound

Product 1

HCID 2736363ethyl 1-(4-aminophenyl)-2-methyl-5-phenylpyrrole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-1-(4-nitro-phenyl)-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester of Example 33 (2 mmol, 0.8 g) was dissolved 50% solution of ethyl acetate in ethanol, and treated with Pd/C (0.088 g). The mixture was hydrogenated with H2 (g) at 45 psi. Upon completion of the reaction, the mixture was filtered through Celite and the solvents removed under vacuum. This material was purified over silica gel to yield the named product.

Workup

  1. customUpon completion of the reaction
  2. filtrationthe mixture was filtered through Celite
  3. customthe solvents removed under vacuum
  4. customThis material was purified over silica gel
  5. customto yield the named product

Sources & evidence

ORD record
ord-6af8119e2a9e488280ef7b1b6af439df
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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