Testosterone → 14958-66-8

HRID 917821Notes

Reaction equation

HRID 917821 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.Cl.[NH2:23][OH:24]>N1C=CC=CC=1>[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18]/[C:16](=[N:23]\[OH:24])/[CH:15]=3

Participants

5

Reactant 2

HCID 6013TestosteroneHCID 443297Hydroxyamine hydrochloride

Product 2

HCID 6013TestosteroneHCID 548820914958-66-8Yield 179.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An oxime of testosterone was prepared in accordance with the following procedure. A dry pyridine solution of testosterone (6.95 mmoles) and hydroxylamine hydrochloride (17.4 mmoles) was stirred at room temperature for 48 hours. The pyridine was removed in vacuo and the crystalline residue was recrystallized from methanol-water and from ethanol to yield 1.89 g (89%) of testosterone oxime, mp 207-210, indicated by tlc to be a mixture of the syn and anti oxime isomers.

Workup

  1. customThe pyridine was removed in vacuo
  2. customthe crystalline residue was recrystallized from methanol-water and from ethanol

Sources & evidence

ORD record
ord-4c27f3bed399454f83eea83dddb7383e
Source dataset
uspto-grants-1976_07
Patent number
US03968105

Reaction notes

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