Sodium → HCID 70416676, compound

HRID 414102Notes

Reaction equation

HRID 414102 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]([CH2:13][C:14](OC)=[O:15])[C:6](=[O:12])[CH2:7][C:8]([O:10][CH3:11])=[O:9].[Na]>CO>[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]1[CH2:13][C:14]([OH:15])=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:6]1=[O:12]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 53686900HCID 53686900, compound

Product 1

HCID 70416676HCID 70416676, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

196.5 g (0.75 mol) of N-(2-methoxycarbonylacetyl)iminodiacetic acid dimethyl ester dissolved in 200 ml of methanol are added dropwise to a solution of 17.1 g of sodium (0.75 mol) in 900 ml of methanol. The reaction mixture is then heated under reflux for 12 hours, cooled to room temperature and concentrated to dryness by evaporation under a water-jet vacuum. The yellowish residue is dissolved in 500 ml of water, filtered over a layer of diatomaceous earth and then 160 ml of semi-concentrated aqueous hydrochloric acid are added. After stirring for a further one hour the resulting crystals are filtered off, washed with acetone and dried. 2,5-dihydro-4-hydroxy-3-methoxycarbonyl-2-oxo-1H-pyrrole-1-acetic acid methyl ester is obtained having a melting point of 192° (decomposition).

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureunder reflux for 12 hours
  3. concentrationconcentrated to dryness by evaporation under a water-jet vacuum
  4. dissolutionThe yellowish residue is dissolved in 500 ml of water
  5. filtrationfiltered over a layer of diatomaceous earth
  6. addition160 ml of semi-concentrated aqueous hydrochloric acid are added
  7. filtrationare filtered off
  8. washwashed with acetone
  9. customdried

Sources & evidence

ORD record
ord-968b19ac9d404566b84af9d8be8727a8
Source dataset
uspto-grants-1988_12
Patent number
US04789674

Reaction notes

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