Ammonia → 4-Azatricyclo(5.2.2.0,2,6)undecane-3,5-dione

HRID 2107998Notes

Reaction equation

HRID 2107998 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]1[C:9](O[C:12](=[O:13])[CH:2]21)=[O:10].[NH3:14].O>O1CCCC1>[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]1[C:9](=[O:10])[NH:14][C:12](=[O:13])[CH:2]21

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 2522504-Oxatricyclo[5.2.2.0,2,6]undecane-3,5-dione

Product 1

HCID 155819864-Azatricyclo(5.2.2.0,2,6)undecane-3,5-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride (3 g; 16.6 mmol) in tetrahydrofuran (9 ml) was dropwise added to a mixture of 29% aqueous ammonia (6 g; 83 mmol) and water (18 ml) while ice-cooling, and the resultant mixture was heated. After removal of the solvent by distillation under an ordinary pressure, acetic anhydride (10 ml) was added thereto, followed by refluxing for 30 minutes. The solvent was removed by distillation under reduced pressure, and the residue was combined with toluene (24 ml) and heated to dissolve. After cooling, the precipitated crystals were collected by filtration to give the objective compound. M.P., 199 -200° C.

Workup

  1. temperaturecooling
  2. customAfter removal of the solvent
  3. distillationby distillation under an ordinary pressure, acetic anhydride (10 ml)
  4. additionwas added
  5. temperatureby refluxing for 30 minutes
  6. customThe solvent was removed by distillation under reduced pressure
  7. temperatureheated to dissolve
  8. temperatureAfter cooling
  9. filtrationthe precipitated crystals were collected by filtration
  10. customto give the objective compound
  11. customM.P., 199 -200° C.

Sources & evidence

ORD record
ord-930f58ef284542179c7f4ec38b3f982c
Source dataset
uspto-grants-1990_06
Patent number
US04937249

Reaction notes

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