Ammonia → Methyl 1-(2-amino-2-oxoethyl)-2,5-dihydro-4-hydroxy-2-oxo-1H-pyrrole-3-carboxylate

HRID 845427Notes

Reaction equation

HRID 845427 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH2:9][C:8]([OH:10])=[C:7]([C:11]([O:13][CH3:14])=[O:12])[C:6]1=[O:15].[NH3:17]>>[OH:10][C:8]1[CH2:9][N:5]([CH2:4][C:3]([NH2:17])=[O:2])[C:6](=[O:15])[C:7]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 70416676HCID 70416676, compound

Product 1

HCID 54716762Methyl 1-(2-amino-2-oxoethyl)-2,5-dihydro-4-hydroxy-2-oxo-1H-pyrrole-3-carboxylate

Procedure

23 g (0.1 mol) of the 2,5-dihydro-4-hydroxy-3-methoxycarbonyl-2-oxo-1H-pyrrole-1-acetic acid methyl ester described in Example 1 are dissolved in 200 ml of a concentrated aqueous ammonia solution and stirred at room temperature for 12 hours. The yellowish solution is then concentrated to dryness by evaporation under a water-jet vacuum. The resulting solid residue is dissolved in 200 ml of water, and a concentrated aqueous solution of hydrochloric acid is added until a strongly acidic reaction takes place. The resulting colourless precipitate is filtered off, washed with water and acetone and dried at 50° under reduced pressure. 2,5-dihydro-4-hydroxy-3-methoxycarbonyl-2-oxo-1H-pyrrole-1-acetamide is obtained in the form of white crystals having a melting point of 202° (decomposition).

Workup

  1. concentrationThe yellowish solution is then concentrated to dryness by evaporation under a water-jet vacuum
  2. dissolutionThe resulting solid residue is dissolved in 200 ml of water
  3. additiona concentrated aqueous solution of hydrochloric acid is added until a strongly acidic reaction
  4. filtrationThe resulting colourless precipitate is filtered off
  5. washwashed with water and acetone
  6. customdried at 50° under reduced pressure

Sources & evidence

ORD record
ord-f9a70dd3021147b5a45a28bd88e5fadb
Source dataset
uspto-grants-1988_07
Patent number
US04758575

Reaction notes

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