Norethindrone → Norethisterone-3-oxime

HRID 917820

Reaction equation

HRID 917820 reaction equation
[CH3:1][C@@:2]12[C@:10]([OH:13])([C:11]#[CH:12])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:14][CH2:15][C:16]3[C@@H:22]([C@H:5]1[CH2:4][CH2:3]2)[CH2:21][CH2:20][C:18](=O)[CH:17]=3.Cl.[NH2:24][OH:25]>N1C=CC=CC=1>[CH3:1][C@@:2]12[C@:10]([OH:13])([C:11]#[CH:12])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:14][CH2:15][C:16]3[C@@H:22]([C@H:5]1[CH2:4][CH2:3]2)[CH2:21][CH2:20]/[C:18](=[N:24]\[OH:25])/[CH:17]=3

Participants

4

Reactant 2

HCID 6230NorethindroneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 9571025Norethisterone-3-oximeYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
98 °C

Procedure

A solution of norethindrone, 6.5 m moles, and hydroxylamine hydrochloride, 16.4 m moles, in 10 ml of dried pyridine was stirred at room temperature for 48 hours. The progress of the reaction was followed by tlc (thin layer chromatography). The reaction mixture was then heated at 98°C. (bath temperature) for 15 minutes, allowed to cool to 55°C and the pyridine was evaporated in vacuo. The residue was extracted with ether. Drying and removal of the ether gave a residue which was recrystallized from methanol-water and methanol to yield 1.93 g (95%) of norethindrone oxime, mp 121.5°-123°C. Tlc with ethyl acetate: petroleum ether; acetone 1:1:0.2 indicated the product to be a mixture of the syn and anti isomers of the oxime.

Workup

  1. temperatureto cool to 55°C
  2. customthe pyridine was evaporated in vacuo
  3. extractionThe residue was extracted with ether
  4. customDrying
  5. customremoval of the ether
  6. customgave a residue which
  7. customwas recrystallized from methanol-water and methanol

Sources & evidence

ORD record
ord-f230b6a7a0994af2aad3ed71b1808606
Source dataset
uspto-grants-1976_07
Patent number
US03968105

Linked notes

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