Sodium ethoxide → 3-Amino-2-ethoxycarbonyl-2-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole

HRID 1457269Notes

Reaction equation

HRID 1457269 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6](C)[CH:7]=[C:8]([C:11]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=1[CH3:19])[C:9]#[N:10])[CH3:2].[O-][CH2:23]C.[Na+]>>[NH2:10][CH:9]1[C:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])=[CH:7][NH:6][C:5]1([C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH3:23]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 54495113N-Methyl-N-[2-(2,4,6-trimethylphenyl)-2-cyanovinyl]-glycine ethyl ester

Product 1

HCID 676451473-Amino-2-ethoxycarbonyl-2-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole

Procedure

A solution of N-Methyl-N-[2-(2,4,6-trimethylphenyl)-2-cyanovinyl]-glycine ethyl ester (6.8 g, 24 mmol) in 0.28M ethanolic sodium ethoxide (100 mL) was heated at 70° C. for 6 h. The reaction was cooled and evaporated in vacuo. The residue was treated with water and neutralized with acetic acid and the product was extracted with ethyl acetate. After drying the solvent was removed in vacuo to afford 3-Amino-2-ethoxycarbonyl-2-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole as a yellow oil.

Workup

  1. temperatureThe reaction was cooled
  2. customevaporated in vacuo
  3. additionThe residue was treated with water and neutralized with acetic acid
  4. extractionthe product was extracted with ethyl acetate
  5. customAfter drying the solvent
  6. customwas removed in vacuo

Sources & evidence

ORD record
ord-3f00fcfeb85945c59c382bd5862b9934
Source dataset
uspto-grants-1998_12
Patent number
US05847136

Reaction notes

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