Hydrochloric Acid → HCID 86738041, compound

HRID 848424Notes

Reaction equation

HRID 848424 reaction equation
[N:1](=[C:3]1[C:9]([CH3:11])([CH3:10])[CH:8]2[C:5]([CH3:13])([CH2:6][CH:7]2[OH:12])[C:4]1=O)[OH:2].O.NN.[OH-].[K+].Cl>C(O)CO.O>[N:1](=[C:3]1[C:9]([CH3:10])([CH3:11])[CH:8]2[C:5]([CH3:13])([CH2:6][CH:7]2[OH:12])[CH2:4]1)[OH:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 867380426-Hydroxy-1,4,4-trimethylbicyclo[3.2.0]heptane-2,3-dione 3-oxime

Product 1

HCID 86738041HCID 86738041, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

To a solution of 2050 mg of the ketoxime (VI) in 25 ml of ethylene glycol, was added 0.7 ml of 80% hydrazine hydrate. After having been kept at 40° to 50° C. for 30 minutes, the solution was admixed with 750 mg of potassium hydroxide and kept at 150° C. for 4 hours under an argon atmosphere. After cooling and adding 50 ml of water, the solution was neutralized with 1 N HCl and extracted with methylene chloride. The extract was washed with an aqueous sodium bicarbonate solution, then with an aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give 970 mg of a crystalline compound (V). M.p. 130°-133° C.; MS m/e: 183 (M+).

Workup

  1. waitkept at 150° C. for 4 hours under an argon atmosphere
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with an aqueous sodium bicarbonate solution
  5. dry with materialwith an aqueous sodium chloride solution, dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81bdb3c6271f425891d340cff9a63ec4
Source dataset
uspto-grants-1981_10
Patent number
US04296036

Reaction notes

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