Ammonia → 1,2,3,4,-5,6-Hexahydro-6-methyl-8-hydroxy-11-oxo-2,6-methano-3-benzazocine

HRID 26278Notes

Reaction equation

HRID 26278 reaction equation
[CH3:1][C:2]12[C:16](=[O:17])[CH:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][C:9]=31)[NH:5][CH2:4][CH2:3]2.N>Br>[CH3:1][C:2]12[C:16](=[O:17])[CH:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=31)[NH:5][CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13452406HCID 13452406, compound

Product 1

HCID 213253611,2,3,4,-5,6-Hexahydro-6-methyl-8-hydroxy-11-oxo-2,6-methano-3-benzazocine

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 1,2,3,4,5,6-hexahydro-6-methyl-8-methoxy-11-oxo-2,6-methano-3-benzazocine (2.18 g.) and hydrobromic acid (48%, 20 ml.) was stirred under reflux (for 30 min.), basified with dilute ammonia and extracted with chloroform. Desiccation and concentration of the chloroform extracts afforded a tan solid (1.1 g.), recrystallization of which from acetone afforded 1,2,3,4,-5,6-hexahydro-6-methyl-8-hydroxy-11-oxo-2,6-methano-3-benzazocine (III: R=CH3, X"=HO, Y+Z=O; 0.4 g.), a white solid.

Workup

  1. temperatureunder reflux (for 30 min.)
  2. extractionextracted with chloroform
  3. customDesiccation and concentration of the chloroform extracts afforded
  4. customa tan solid (1.1 g.), recrystallization of which from acetone

Sources & evidence

ORD record
ord-9798e94fd6654119b5add31bf982b1e0
Source dataset
uspto-grants-1979_04
Patent number
US04149000

Reaction notes

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