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

HRID 1252686Notes

Reaction equation

HRID 1252686 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]>O1CCCC1.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

5

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 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of bicyclo[2.2.2]octane-2,3dicarboxylic anhydride (3 g; 16.6 mmol) in tetrahydrofuran (9 ml) was dropwise added to a mixture of 29% aqueous ammonia (6 g; 83 mmol) in water (18 ml) while ice-cooling, and the resultant mixture was heated. The solvent was removed under atmospheric pressure, and acetic anhydride (10 ml) was added thereto, followed by refluxing for 30 minutes. The solvent was removed 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. customThe solvent was removed under atmospheric pressure, and acetic anhydride (10 ml)
  3. additionwas added
  4. temperatureby refluxing for 30 minutes
  5. customThe solvent was removed under reduced pressure
  6. temperatureheated to dissolve
  7. temperatureAfter cooling
  8. filtrationthe precipitated crystals were collected by filtration
  9. customto give the objective compound
  10. customM.P., 199°-200° C.

Sources & evidence

ORD record
ord-c466efb4d3284b2682105aa0cbd68fd7
Source dataset
uspto-grants-1988_05
Patent number
US04745117

Reaction notes

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