Methyl iodide → Ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

HRID 850973Notes

Reaction equation

HRID 850973 reaction equation
[CH3:1][O-].[Na+].[N+:4]([C:7]1[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:10][CH:11]=1)([O-:6])=[O:5].CI>CO>[CH3:1][N:10]1[CH:11]=[C:7]([N+:4]([O-:6])=[O:5])[CH:8]=[C:9]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 242169Ethyl 4-Nitropyrrole-2-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 10442704Ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
35 °C

Procedure

A solution of 2.5 g. of sodium methoxide in 25 ml. of methanol is cooled to 10° C. and a mixture of 7.0 g. of ethyl 4-nitro-2-pyrrolecarboxylate in 15 ml. of methanol is added. After 10 minutes, 18.6 g. of methyl iodide is added. The dark-colored solution is warmed to 35° C. for 0.5 hours, then cooled and allowed to stir at room temperature for 16 hours. Chilling and filtration affords a solid which is collected by filtration and recrystallized from ethanol to yield the product.

Workup

  1. additiona mixture of 7.0 g
  2. temperaturecooled
  3. temperatureChilling
  4. filtrationfiltration
  5. customaffords a solid which
  6. filtrationis collected by filtration
  7. customrecrystallized from ethanol
  8. customto yield the product

Sources & evidence

ORD record
ord-ca9ef00cb187429cbafb22fc50d52524
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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