Ammonium Acetate → methyl 2-{2-amino-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylate

HRID 733716Notes

Reaction equation

HRID 733716 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH3:10])[C:6]=1[C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12]O)=[O:4].C([O-])(=O)C.[NH4+:22]>CO>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH3:10])[C:6]=1[C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][NH2:22])=[O:4]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 68867490Methyl 2-{2-hydroxy-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 68866598methyl 2-{2-amino-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylateYield 26.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-Hydroxy-1-methoxycarbonyl-vinyl)-1-methyl-1H-pyrrole-3-carboxylic acid methyl ester (12.46 g), ammonium acetate (20.09 g) and methanol (200 ml) were refluxed under argon for 5 hours. After cooling the solvent was evaporated and the residue dissolved in ethyl acetate and washed with water, the aqueous was separated and extracted three times with ethyl acetate. The combined organics were washed with saturated brine solution and the organic layer was dried (MgSO4), filtered and evaporated. The residue was then taken up in the minimum amount of ethyl acetate and a precipitate formed which was filtered off to yield the title compound as an off-white solid (3.3 g). The filtrate was evaporated to yield the title compound as a brown solid (6.36 g). Both were taken through without further purification.

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water
  5. customthe aqueous was separated
  6. extractionextracted three times with ethyl acetate
  7. washThe combined organics were washed with saturated brine solution
  8. dry with materialthe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customa precipitate formed which
  12. filtrationwas filtered off

Sources & evidence

ORD record
ord-17a7d7e2d8d248cda8ddfd5af9b3970a
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

Loading…