Triazabicyclodecene → 4-methyl-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2427407Notes

Reaction equation

HRID 2427407 reaction equation
N12CCCNC1=NCCC2.[CH3:11][C:12]1[CH:24]=[CH:23][C:15]([CH:16]=[C:17]([CH2:21]C)[N+]([O-])=O)=[CH:14][CH:13]=1.[CH2:25]([O:27][C:28](=[O:32])[CH2:29][N+:30]#[C-:31])[CH3:26]>C(O)(C)C.C1COCC1>[CH2:25]([O:27][C:28]([C:29]1[NH:30][CH:31]=[C:17]([CH3:21])[C:16]=1[C:15]1[CH:23]=[CH:24][C:12]([CH3:11])=[CH:13][CH:14]=1)=[O:32])[CH3:26]

Participants

6

Reactant 3

HCID 79873TriazabicyclodeceneHCID 533707Ethyl isocyanoacetateHCID 668835694-Methyl-beta-ethyl-beta-nitrostyrene

Product 1

HCID 156132434-methyl-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,5,7-Triazabicyclo[4.4.0]dec-5-ene on polystyrene (5.36 g, 2.6 mmol/g, 13.9 mmol) was added to a reaction mixture of 4-methyl-β-ethyl-β-nitrostyrene (1.23 g, 6.94 mmol) and isocyanoacetic acid ethyl ester (788 mg, 6.90 mmol) in isopropanol (5 mL) and THF (5 mL) and the reaction mixture was stirred overnight at RT under nitrogen as protective gas. The reaction mixture was filtered out and the residue washed with isopropanol and THF. The desired product 4-methyl-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.42 g, 85% of theoretical) was obtained.

Workup

  1. filtrationThe reaction mixture was filtered out
  2. washthe residue washed with isopropanol and THF

Sources & evidence

ORD record
ord-eea1f965d4cf40fe8f05ff38e951ec8b
Source dataset
uspto-grants-2011_06
Patent number
US07968591B2

Reaction notes

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