Hydrochloric Acid → 3-Azaspiro(5.5)undecane-2,4-dione

HRID 130579Notes

Reaction equation

HRID 130579 reaction equation
C([CH:3]1[C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7](C(OC)=O)[C:6](=[O:18])[NH:5][C:4]1=[O:19])#N.[OH-].[Na+].Cl>C(O)C.O>[O:19]=[C:4]1[NH:5][C:6](=[O:18])[CH2:7][C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11323033Methyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate

Product 1

HCID 143243-Azaspiro(5.5)undecane-2,4-dioneYield 68.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
20 °C

Procedure

10 g of methyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate and 5 g of NaOH dissolved in 125 ml of 2:1 ethanol/water are placed in a 250 ml flask equipped with mechanical agitator, thermometer and condenser. The mixture is heated under reflux for 1.5 hours, acidified with 5% HCl to pH 2 and heated under reflux for 3 hours. By cooling to 20° C. a precipitate is formed which is filtered off, washed with water and dried under vacuum. 4.7 g of 2,4-dioxo-3-azaspiro[5,5]undecane are obtained.

Workup

  1. customare placed in a 250 ml flask
  2. customequipped with mechanical agitator
  3. temperatureThe mixture is heated
  4. temperatureunder reflux for 1.5 hours
  5. temperatureheated
  6. temperatureunder reflux for 3 hours
  7. customis formed which
  8. filtrationis filtered off
  9. washwashed with water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-1b865930ef554f46af6702e236808c8f
Source dataset
uspto-grants-2008_06
Patent number
US07381823B2

Reaction notes

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