ethyl 2-chloro-1-methyl-5-phenyl-1H-pyrrole-3-carboxylate → Ethyl 5-phenyl-1H-pyrrole-3-carboxylate

HRID 339726Notes

Reaction equation

HRID 339726 reaction equation
Cl[C:2]1[N:3](C)[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>CO.[Pd]>[C:12]1([C:4]2[NH:3][CH:2]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 11832263ethyl 2-chloro-1-methyl-5-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 10242379Ethyl 5-phenyl-1H-pyrrole-3-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 2-chloro-1-methyl-5-phenyl-1H-pyrrole-3-carboxylate (2.4 g, 9.1 mmol) and 10% Pd/C (100 mg) was dissolved in methanol (50 ml) at room temperature. The reaction mixture was hydrogenated for 6 hrs at room temperature and the resulting solution was filtered. After evaporated under reduced pressure, the residue was purified with normal phase preparative column chromatography to produce title compound (1.9g, 91%) as white solid.

Workup

  1. filtrationthe resulting solution was filtered
  2. customAfter evaporated under reduced pressure
  3. customthe residue was purified with normal phase preparative column chromatography

Sources & evidence

ORD record
ord-12bd385e253842538f585ceee5c28163
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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