Ammonium Acetate → Methyl 2-{(Z)-2-amino-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylate
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
Product 1
Reagents, catalysts & solvents 1
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).