Ammonium Hydroxide → HCID 13714630, compound

HRID 1607495Notes

Reaction equation

HRID 1607495 reaction equation
Cl[C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[CH2:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22].[NH4+:23].[OH-]>O1CCOCC1>[NH2:23][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[CH2:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 14682342HCID 14682342, compound

Product 1

HCID 13714630HCID 13714630, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloroandrost-4-ene-3,17-dione (1.93 g, 6 mmole), dioxane (60 ml) and 30% NH4OH aqueous solution (120 ml) is stirred at room temperature during 24 hours. The organic solvent and excess of ammonia are evaporated in vacuo and the resulting aqueous residue is acidified to pH 1 by carefully adding conc. HCl. The aqueous solution is washed twice with ethyl acetate and brought to pH 11 by carefully adding conc. NaOH. The resulting precipitate is filtered off, washed with water and dried under vacuum at 40° C. There are obtained 559 mg (1.86 mmole, 31% yield) of the title compound as a white solid.

Workup

  1. customThe organic solvent and excess of ammonia are evaporated in vacuo
  2. washThe aqueous solution is washed twice with ethyl acetate
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with water
  5. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-890a160f3b3c4d37830cbdd2b5e08cf9
Source dataset
uspto-grants-1989_09
Patent number
US04865766

Reaction notes

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