Ethyl 4-methyl-3-(2-nitrophenyl)-1H-pyrrole-2-carboxylate → HCID 178430818, compound

HRID 1423360Notes

Reaction equation

HRID 1423360 reaction equation
[CH3:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)=[C:4]([C:7](OCC)=[O:8])[NH:5][CH:6]=1>CC(O)=O.[Fe]>[CH3:1][C:2]1[C:3]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]=[C:7]([OH:8])[C:4]=2[NH:5][CH:6]=1

Participants

4

Reactant 1

HCID 15926189Ethyl 4-methyl-3-(2-nitrophenyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 178430818HCID 178430818, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of ethyl 4-methyl-3-(2-nitrophenyl)-1H-pyrrole-2-carboxylate (3.2 g, 11.67 mmol) in AcOH (117 mL) was treated at 20° C. with iron dust (6.52 g, 117 mmol). The reaction mixture was heated at 100° C. for 3 h. The white precipitate was removed by filtration and the filtrates were concentrated to give a residue that was purified on silica gel (gradient elution, 50-100% MeOH/Acetone) to afford the title compound (2.0 g, 86%) as a solid. LCMS (ES+) m/z 199 (M+H)+.

Workup

  1. customThe white precipitate was removed by filtration
  2. concentrationthe filtrates were concentrated
  3. customto give a residue that
  4. customwas purified on silica gel (gradient elution, 50-100% MeOH/Acetone)

Sources & evidence

ORD record
ord-acae0595263b47cb9ee44f5ba80dae74
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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