Hydrazine → 1,3,3-Trimethyl-2-oxabicyclo [2,2,2]octan-5,6-dione-5-oxime-6-hydrazone

HRID 903615Notes

Reaction equation

HRID 903615 reaction equation
[CH3:1][C:2]12[CH2:12][CH2:11][CH:5]([C:6](=[N:9][OH:10])[C:7]1=O)[C:4]([CH3:14])([CH3:13])[O:3]2.[NH2:15][NH2:16]>C(O)C>[CH3:1][C:2]12[CH2:12][CH2:11][CH:5]([C:6](=[N:9][OH:10])[C:7]1=[N:15][NH2:16])[C:4]([CH3:14])([CH3:13])[O:3]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 867366601,3,3-Trimethyl-2-oxabicyclo[2,2,2]octan-5,6-dione-5-oxime

Product 1

HCID 1363988141,3,3-Trimethyl-2-oxabicyclo [2,2,2]octan-5,6-dione-5-oxime-6-hydrazone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.97 g. (0.01 mole) 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octan-5,6-dione-5-oxime and 0.35 ml. (0.011 mole) anhydrous hydrazine (98%) in 25 ml. absolute ethanol is refluxed under nitrogen at a bath temperature of 80° C. for 1 hour. After evaporation of the solvent, the residue is recrystallized from ether to give 1,3,3-trimethyl-2-oxabicyclo [2,2,2]octan-5,6-dione-5-oxime-6-hydrazone; mp. 138° to 142° C.

Workup

  1. additionA mixture of 1.97 g
  2. customAfter evaporation of the solvent
  3. customthe residue is recrystallized from ether

Sources & evidence

ORD record
ord-963da34727af4e96ac7f2f01ed8ac29c
Source dataset
uspto-grants-1980_10
Patent number
US04228280

Reaction notes

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