Hydrazine → HCID 15586932, compound

HRID 225194Notes

Reaction equation

HRID 225194 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([CH2:18]OS(C)(=O)=O)[CH2:3]1.[NH2:24][NH2:25]>>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([CH2:18][NH:24][NH2:25])[CH2:3]1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 86737357HCID 86737357, compound

Product 1

HCID 15586932HCID 15586932, compoundYield 71%

Conditions

Temperature
150 °C

Procedure

5 g (0.0146 moles) of 6-methyl-8β-mesyloxymethyl-ergoline are suspended in 25 ml of dry hydrazine distilled from sodium hydroxide. The suspension is refluxed under a nitrogen atmosphere on an oil bath heated to 150° C. for 20 minutes after the complete dissolution of the solids. In this operation atmospheric moisture should be excluded carefully. The mixture is cooled and allowed to stand in a refrigerator. The separated crystals are filtered off, washed with water, and then dried in vacuo. 2.8 g (71%) of 6-methyl-8β-hydrazinomethyl-ergoline are obtained; m.p.: 171°-172° C., [α]D20 =-62.8° (c=0.2, in tetrahydrofuran).

Workup

  1. distillationdistilled from sodium hydroxide
  2. temperatureThe suspension is refluxed under a nitrogen atmosphere on an oil bath
  3. dissolutionafter the complete dissolution of the solids
  4. temperatureThe mixture is cooled
  5. filtrationThe separated crystals are filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-55a4378e7dbb4ff3bb073634df335813
Source dataset
uspto-grants-1980_11
Patent number
US04235912

Reaction notes

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