Toluene → HCID 12286599, compound

HRID 1580132Notes

Reaction equation

HRID 1580132 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:17][CH:13]([NH:14][C:15]2=[O:16])[C:12](=NN)[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:17][CH:13]([NH:14][C:15]2=[O:16])[CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 23665647Potassium tert-butoxideHCID 68145452HCID 68145452, compound

Product 1

HCID 12286599HCID 12286599, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21.73 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione, 4.9 g of hydrazine hydrate and 170 ml of ethanol is refluxed for 1 hour. After cooling, the mixture is evaporated under reduced pressure to remove solvent. The residue thus obtained is dispersed in benzene and then filtered to give 21.64 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione-4-hydrazone as crude crystals. A mixture of 21.64 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione-4-hydrazone, 17.1 g of potassium tert.-butoxide and 400 ml of toluene is refluxed for 2 hours under heating. After cooling, water is added to the mixture, and the aqueous mixture is extracted with ether. The ether extract is washed with water, dried and then evaporated to remove solvent. The residue thus obtained is recrystallized from a mixture of ethylacetate and n-hexane. 17.54 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-7-one are obtained. M.p. 109° - 111°C.

Workup

  1. temperatureis refluxed for 2 hours
  2. temperatureunder heating
  3. temperatureAfter cooling
  4. extractionthe aqueous mixture is extracted with ether
  5. extractionThe ether extract
  6. washis washed with water
  7. customdried
  8. customevaporated
  9. customto remove solvent
  10. customThe residue thus obtained
  11. customis recrystallized from a mixture of ethylacetate and n-hexane

Sources & evidence

ORD record
ord-359e53422df1401f88dfa54ef5ee5b1f
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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