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 2299256Notes

Reaction equation

HRID 2299256 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-(2,4,6trimethylphenyl)-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-1b2d023fe30b46839f058a38611c9b40
Source dataset
uspto-grants-2002_12
Patent number
US06495688B2

Reaction notes

Loading…