Methanol → Methyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

HRID 908141Notes

Reaction equation

HRID 908141 reaction equation
OS(O)(=O)=O.[CH3:6][N:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]1[C:15]([OH:17])=[O:16].O.[CH3:19]O>>[CH3:6][N:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]1[C:15]([O:17][CH3:19])=[O:16]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 27369151-Methyl-4-nitropyrrole-2-carboxylic acid

Product 1

HCID 2759930Methyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

Procedure

A cold solution of H2SO4 (2.9 mL) in MeOH (28.96 mL) was added to 1-methyl-4-nitropyrrole-2-carboxylic acid (2.897 g, 2.35 mmol). The mixture was refluxed for 24 hr. Water was added and the mixture extracted CHCl3. The organic layer was dried (MgSO4), and the solvent evaporated under vacuum to afford the creamy white product. NMR as previously reported.

Workup

  1. temperatureThe mixture was refluxed for 24 hr
  2. extractionthe mixture extracted CHCl3
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent evaporated under vacuum
  5. customto afford the creamy white product

Sources & evidence

ORD record
ord-27ada8a908fc4c64bff66478a3ebd3e8
Source dataset
uspto-grants-2011_09
Patent number
US08017599B2

Reaction notes

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