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

HRID 1193988Notes

Reaction equation

HRID 1193988 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>[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

4

Reactant 2

HCID 222AmmoniaHCID 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 962WaterSolvent

Procedure

A solution of bicyclo[2.2.2]octane-2,3-dicarboxylic anhydride (3 g; 16.6 mmol) in tetrahydrofurn (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-1e0f6d2b9fa24fc281351a739994ba69
Source dataset
uspto-grants-1989_03
Patent number
US04812461

Reaction notes

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