Water → 3-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-ene

HRID 1871911Notes

Reaction equation

HRID 1871911 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:17][CH:16]2[N:18](C(OCC)=O)[CH:13]([CH2:14][CH2:15]2)[CH:12]=1.O.NN.[OH-].[K+].O>C(O)CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:12][CH:13]2[NH:18][CH:16]([CH2:15][CH2:14]2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 186899033-(Naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]oct-2-ene

Product 1

HCID 119560113-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-ene

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 5.0 gm (16.3 mMol) 3-(naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]oct-2-ene, 4.07 gm (81.3 mMol) hydrazine hydrate, and 5.49 gm (97.8 mMol) potassium hydroxide in 120 mL ethylene glycol was heated at reflux for 2 hours. The reaction mixture was allowed to cool gradually to room temperature. After 16 hours the reaction mixture was poured into water and extracted well with diethyl ether. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The residue was dissolved in 1N hydrochloric acid and the solution washed with diethyl ether. The aqueous phase was basified and the mixture extracted well with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated under reduced pressure to provide the title compound as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted well with diethyl ether
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 1N hydrochloric acid
  7. washthe solution washed with diethyl ether
  8. extractionthe mixture extracted well with ethyl acetate
  9. dry with materialThe organic phase was dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92b3ebec8e9c4e1cbc5af45f30232fdb
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

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