4-Aminobenzoic Acid → 2-Azabicyclo(2.2.2)octan-3-one

HRID 1656052Notes

Reaction equation

HRID 1656052 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1>O.[Rh]>[CH2:4]1[CH:5]2[C:6]([NH:1][CH:2]([CH2:10][CH2:9]2)[CH2:3]1)=[O:7]

Participants

4

Reactant 1

HCID 9784-Aminobenzoic Acid

Product 1

HCID 1378872-Azabicyclo(2.2.2)octan-3-one

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 962WaterSolvent2×

Procedure

Suspend 5% rhodium/carbon (2 g) in water (50 mL) and add 4-aminobenzoic acid (27.4 g, 200 mmol) and dilute to 200 mL with water. Shake the mixture at 50 psi for 4 days, filter through glass fiber and evaporate the solvent in vacuo to a white solid. Mix the solid with diphenyl ether and heat quickly to reflux for 20 minutes. Cool and partition between hexane and water. Separate the organic phase and wash with water. Combine the aqueous phases, treat with sodium hydrogen carbonate and subject to continuous extraction with methylene chloride overnight. Evaporate the methylene chloride extracts in vacuo to give 3-isoquinuclidone as a white solid.

Workup

  1. filtrationfilter through glass fiber
  2. customevaporate the solvent in vacuo to a white solid
  3. additionMix the solid with diphenyl ether
  4. temperatureheat quickly
  5. temperatureto reflux for 20 minutes
  6. temperatureCool
  7. custompartition between hexane and water
  8. customSeparate the organic phase
  9. washwash with water
  10. additiontreat with sodium hydrogen carbonate
  11. extractionsubject to continuous extraction with methylene chloride overnight
  12. customEvaporate the methylene chloride

Sources & evidence

ORD record
ord-90b45494310f4cc6b55b9c0553772028
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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