Hydrochloric Acid → HCID 13711992, compound

HRID 620866Notes

Reaction equation

HRID 620866 reaction equation
C(O[C:4]1([CH2:12][C:13]([O:15]CC)=O)[CH2:8][C:7](=[O:9])[NH:6][C:5]1=C=O)C.[OH-:18].[Na+].Cl>>[CH2:5]([N:6]1[C:13](=[O:15])[CH2:12][C:4]2([CH2:8][C:7](=[O:9])[NH:6][CH2:5]2)[C:7]1=[O:18])[CH3:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86742947HCID 86742947, compound

Product 1

HCID 13711992HCID 13711992, compound

Procedure

A suspension of 24.3 g (0.10 mmole) 3-ethoxy-carbonyl-5-oxo-3-pyrrolidineacetic acid, ethyl ester in an excess of 2 N sodium hydroxide, was stirred three hours at room temperature, acidified with dilute hydrochloric acid, and evaporated to dryness in vacuo. The product, 3-carboxy-5-oxo3-pyrrolidineacetic acid, was taken up in isopropyl alcohol, separated from insoluble sodium chloride by filtration, concentrated to a syrup and dissolved in 100 ml 70% ethylamine. The solution was gradually heated in an oil bath up to 230° C. allowing volatiles to distill and then maintained at 230°-240° C. for ten minutes. After cooling, the product was crystallized from isopropyl alcohol to afford 10.1 g of 2-ethyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione, mp 168°-169° C.

Workup

  1. customevaporated to dryness in vacuo
  2. customseparated from insoluble sodium chloride by filtration
  3. concentrationconcentrated to a syrup
  4. dissolutiondissolved in 100 ml 70% ethylamine
  5. temperatureThe solution was gradually heated in an oil bath up to 230° C.
  6. distillationto distill
  7. temperaturemaintained at 230°-240° C. for ten minutes
  8. temperatureAfter cooling
  9. customthe product was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-f66c5367a7ee4bd8984f45959546b5e6
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

Loading…