Ammonium Hydroxide → 5-oxopyrrolidine-2-carboxamide

HRID 1980247Notes

Reaction equation

HRID 1980247 reaction equation
[NH2:1][C@H:2]([C:10]([O:12]CC)=O)[CH2:3][CH2:4][C:5](OCC)=[O:6].[OH-].[NH4+:16]>>[NH:1]1[CH:2]([C:10]([NH2:16])=[O:12])[CH2:3][CH2:4][C:5]1=[O:6]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 73961Glutamic acid diethyl ester

Product 1

HCID 2204615-oxopyrrolidine-2-carboxamideYield 78.6%

Procedure

A mixture of 575 g diethyl glutamate and 700 ml concentrated ammonium hydroxide was stirred for 10 hours, and kept in the freezer at (-20° C.) for 5 hours. The resulting white crystalline solid was filtered, washed with 500 ml ethanol followed by 200 ml ether and dried in a vacuum oven at 70° C. for 16 hours to remove the water of crystallization giving 270 g (78.6%) of white crystalline 2-pyrrolidone-5-carboxamide.

Workup

  1. waitkept in the freezer at (-20° C.) for 5 hours
  2. filtrationThe resulting white crystalline solid was filtered
  3. washwashed with 500 ml ethanol
  4. customdried in a vacuum oven at 70° C. for 16 hours
  5. customto remove
  6. customthe water of crystallization

Sources & evidence

ORD record
ord-52a4d281a4d646c5969c417e73268cb5
Source dataset
uspto-grants-1985_04
Patent number
US04508725

Reaction notes

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