Ammonium Hydroxide → 4-Aminoandrosta-1,4,6-Triene-3,17-Dione

HRID 1607498Notes

Reaction equation

Cl[C:2]1[C:19](=[O:20])[CH:18]=[CH:17][C@@:16]2([CH3:21])[C:3]=1[CH:4]=[CH: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])[CH:18]=[CH:17][C@@:16]2([CH3:21])[C:3]=1[CH:4]=[CH: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

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-chloroandrosta-1,4,6-triene-3,17-dione (1.585 g, 5 mmole), dioxane (50 ml) and 30% NH4OH aqueous solution (100 ml) is stirred at 90° C. in a pressure vessel during 24 hours. After cooling to room temperature, the reaction mixture is worked up as described in the Example I. There are obtained 370 mg (1.24 mmole, 24% yield ) of the title compound or a yellow solid.

Workup

temperatureAfter cooling to room temperature

Sources & evidence

ORD record: ord-ef81dbc289474973a9a90a3ecc11f443
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04865766

Reaction notes

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