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

HRID 733689Notes

Reaction equation

HRID 733689 reaction equation
O[CH:2]=[C:3]([C:8]1[N:9]([CH3:17])[CH:10]=[CH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14])[C:4]([O:6][CH3:7])=[O:5].C([O-])(=O)C.[NH4+:22]>CO>[NH2:22]/[CH:2]=[C:3](/[C:8]1[N:9]([CH3:17])[CH:10]=[CH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14])\[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

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

Product 1

HCID 57840846Methyl 2-{(Z)-2-amino-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylateYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-{2-hydroxy-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylate (65.2 g) and ammonium acetate (105 g) in methanol (800 ml) was heated at reflux for 7 hours. The reaction was cooled and the methanol removed. The residue was partitioned between ethyl acetate and water. Large amounts (>2 L) of ethyl acetate were used to dissolve the residue. The organic solution washed with water, dried (MgSO4) and the solvent removed to yield the title compound as a brown solid (58.4 g).

Workup

  1. temperatureat reflux for 7 hours
  2. temperatureThe reaction was cooled
  3. customthe methanol removed
  4. customThe residue was partitioned between ethyl acetate and water
  5. dissolutionto dissolve the residue
  6. washThe organic solution washed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed

Sources & evidence

ORD record
ord-d634de2f49a44b89ade6e05fac776a1f
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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