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

HRID 908139Notes

Reaction equation

HRID 908139 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

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 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).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 hr
  3. extractionthe mixture extracted with DCM
  4. customThe organic solvent was dried
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-54024aab64fa475b9dbd88785017b824
Source dataset
uspto-grants-2011_09
Patent number
US08017599B2

Reaction notes

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