Hydrazine → HCID 86734262, compound

HRID 1973498Notes

Reaction equation

HRID 1973498 reaction equation
[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][C:21](=O)[C@@:20]4([CH3:24])[C@@H:11]([CH2:12][CH2:13][C:14]5[CH:15]=[C:16]([O:25][CH3:26])[CH:17]=[CH:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1.Cl.Cl.NN.O.NN.[OH-].[K+].NN>C(O)COCCOCCO.O>[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][CH2:21][C@@:20]4([CH3:24])[C@@H:11]([CH2:12][CH2:13][C:14]5[CH:15]=[C:16]([O:25][CH3:26])[CH:17]=[CH:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1

Participants

8

Reactant 5

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 17548Hydrazine, dihydrochlorideHCID 24654Hydrazine hydrate (1:1)HCID 86734261HCID 86734261, compound

Product 1

HCID 86734262HCID 86734262, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8172Triethylene GlycolSolvent

Procedure

A mixture of 534 mg of 17-ethylenedioxy-3-methoxy-9α-methylestra-1,3,5-(10)-trien-11-one, 1 g of hydrazine dihydrochloride and 5 g of hydrazine hydrate in 35 g of triethyleneglycol is heated to a temperature of 130° and maintained there for 21/2 hours. After this time, 1.8 g of potassium hydroxide pellets is added and the temperature raised to 210°. This temperature is also maintained for 21/2 hours whilst a mixture of hydrazine and water is slowly allowed to distill out. The reaction mixture is cooled and diluted with water affording a precipitate which is collected by filtration. The solid is dissolved in methylene chloride and the organic solution is dried over sodium sulfate. Removal of the solvent leaves a residue which is crystallized from hexane-ether to yield 17-ethylenedioxy-3-methoxy-9α-methylestra-1,3,5(10)-triene, m.p. 115° C.

Workup

  1. temperatureis heated to a temperature of 130°
  2. temperaturemaintained there for 21/2 hours
  3. temperaturethe temperature raised to 210°
  4. temperatureThis temperature is also maintained for 21/2 hours
  5. distillationto distill out
  6. temperatureThe reaction mixture is cooled
  7. additiondiluted with water affording a precipitate which
  8. filtrationis collected by filtration
  9. dissolutionThe solid is dissolved in methylene chloride
  10. dry with materialthe organic solution is dried over sodium sulfate
  11. customRemoval of the solvent
  12. customleaves a residue which
  13. customis crystallized from hexane-ether

Sources & evidence

ORD record
ord-159ca4f7aa104b4b9d036d7985a10145
Source dataset
uspto-grants-1976_12
Patent number
US03997574

Reaction notes

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