Sodium Hydroxide → HCID 86736928, compound

HRID 2049485Notes

Reaction equation

HRID 2049485 reaction equation
[OH:1][C@@H:2]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:17]2[C:16](=O)[CH2:15][C@@:14]2([CH3:23])[C@H:8]3[CH2:9][CH2:10]/[C:11]/2=[CH:12]/[CH3:13])[CH2:3]1.Cl.[NH2:25][OH:26].[OH-].[Na+]>O>[OH:1][C@@H:2]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:17]2[C:16](=[N:25][OH:26])[CH2:15][C@@:14]2([CH3:23])[C@H:8]3[CH2:9][CH2:10]/[C:11]/2=[CH:12]/[CH3:13])[CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 443297Hydroxyamine hydrochloride2×HCID 12796513HCID 12796513, compound

Product 1

HCID 86736928HCID 86736928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Procedure

A solution of (Z)-3α-hydroxy-5α-pregn-17(20)-en-11-one (10.264 g) in warm industrial methylated spirits (320 ml) was heated with hydroxylamine hydrochloride (3.25 g) and sodium hydroxide (5.123 g) in water (10 ml). The mixture was refluxed for 41 hours and, after addition of more hydroxylamine hydrochloride (15.35 g) in water (20 ml) and sodium hydroxide (25.04 g) in water (50 ml) refluxing was continued for a further 6 hours. The mixture was then poured into water and the crystalline material (10.419 g) collected by filtration. Crystallisation of a portion from aqueous ethanol afforded an analytical sample of title compound m.p. 233°-235°.

Workup

  1. temperatureThe mixture was refluxed for 41 hours
  2. temperaturerefluxing
  3. filtrationthe crystalline material (10.419 g) collected by filtration
  4. customCrystallisation of a portion from aqueous ethanol

Sources & evidence

ORD record
ord-19843aa271834d94920fd272da200a7e
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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