N-Methyl-N-[2-(2,4,6-trimethylphenyl)-2-cyanovinyl]-glycine ethyl ester → 3-Amino-2-ethoxycarbonyl-1-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole

HRID 2393197Notes

Reaction equation

HRID 2393197 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]([CH3:20])[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-]CC.[Na+]>[NH2:10][C:9]1[C:8]([C:11]2[C:12]([CH3:19])=[CH:13][C:14]([CH3:18])=[CH:15][C:16]=2[CH3:17])=[CH:7][N:6]([CH3:20])[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:21]

Participants

3

Reactant 1

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

Product 1

HCID 158867043-Amino-2-ethoxycarbonyl-1-methyl-4-(2,4,6-trimethylphenyl)-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

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-1-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-220be193e124413a9e42c98a799fdf80
Source dataset
uspto-grants-1998_09
Patent number
US05804685

Reaction notes

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