Methanol → Methyl 4-nitro-1h-pyrrole-2-carboxylate

Reaction equation

OS(O)(=O)=O.C[C:7]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][NH:9][C:8]=1[C:15]([OH:17])=[O:16].O.[CH3:19]O>>[CH3:19][O:17][C:15]([C:8]1[NH:9][CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[CH:7]=1)=[O:16]

Participants

Reactant 4

HCID 887Methanol

HCID 962Water

HCID 1118Sulfuric Acid

HCID 53700357Methyl-4-nitropyrrole-2-carboxylic acid

Product 1

HCID 261887Methyl 4-nitro-1h-pyrrole-2-carboxylate

Procedure

A solution of H2SO4 (0.8 mL) in MeOH (8 mL) was added to Py-1 (0.77 g, 4.53 mmol) and the mixture heated at reflux for 24 hr. Water was added and the mixture extracted with DCM. The organic solvent was dried using MgSO4, and solvent evaporated under vacuum to yield the product as a crystalline solid. Yield 0.55 g, 66%). 1H NMR (DMSO): δ 7.57 (d, 1H, J=2.1 Hz); 7.40 (d, 1H, J=2.0 Hz); 3.99 (s, 3H); 3.86 (s, 3H).