1H-Pyrrole-2,4-dicarboxylic acid, 1,3,5-trimethyl-, diethyl ester → 5-ethoxycarbonyl-1,2,4-trimethylpyrrole-3-carboxylic acid

HRID 127601Notes

Reaction equation

HRID 127601 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:18])[C:8]([CH3:17])=[C:9]([C:12]([O:14]CC)=[O:13])[C:10]=1[CH3:11])=[O:5])[CH3:2]>S(=O)(=O)(O)O>[CH3:18][N:7]1[C:8]([CH3:17])=[C:9]([C:12]([OH:14])=[O:13])[C:10]([CH3:11])=[C:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

3

Reactant 1

HCID 2267561H-Pyrrole-2,4-dicarboxylic acid, 1,3,5-trimethyl-, diethyl ester

Product 1

HCID 3437565-ethoxycarbonyl-1,2,4-trimethylpyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The starting material is prepared as follows: The mixture of 11.9 g of 1,3,5-trimethylpyrrole-2,4-dicarboxylic acid diethyl ester and 50 ml of concentrated sulfuric acid is heated on the steam cone for 1 hour. The resulting solution is poured on to ice, the precipitate collected and washed with water. It it taken up in aqueous sodium carbonate, the solution filtered and the filtrate acidified with 5 N hydrochloric acid. The precipitate formed is collected, washed with water, dried and recrystallized from ethanol, to yield the 1,3,5-trimethyl-2-carbethoxypyrrole-4-carboxylic acid melting at 197°-198° with decomposition.

Workup

  1. customThe starting material is prepared
  2. temperatureis heated on the steam cone for 1 hour
  3. additionThe resulting solution is poured on to ice
  4. customthe precipitate collected
  5. washwashed with water
  6. filtrationthe solution filtered
  7. customThe precipitate formed
  8. customis collected
  9. washwashed with water
  10. customdried
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5227082544d54f6cb71df3bc0431d122
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Reaction notes

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