Ammonia → HCID 68147319, compound

HRID 1658703Notes

Reaction equation

HRID 1658703 reaction equation
[FH:1].[CH3:2][C@:3]12[CH2:20][CH:19]=[C:18]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@:16]3([CH3:17])[CH2:15][CH2:14][C:13](=[O:21])[CH:12]=4)[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22].[Cl:23]N1C(=O)CCC1=O.N>CC(C)=O.CCCCCC.CN1CCCC1=O>[Cl:23][C@:18]12[C@@H:19]([F:1])[CH2:20][C@@:3]3([CH3:2])[C@@H:7]([CH2:6][CH2:5][C:4]3=[O:22])[C@@H:8]1[CH2:9][CH2:10][C:11]1[C@:16]2([CH3:17])[CH2:15][CH2:14][C:13](=[O:21])[CH:12]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14917Hydrofluoric AcidHCID 31398ChlorosuccinimideHCID 2395959-Dehydroandrostenedione

Product 1

HCID 68147319HCID 68147319, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 21880519Acetone hexaneSolvent

Procedure

At -78°, a mixture of 15 ml. of hydrogen fluoride and 5 ml. of N-methylpyrrolidone is combined successively with 5.1 g of 4,9(11)-androstadiene-3,17-dione and 10 g. of N-chlorosuccinimide. The reaction solution is allowed to stand for 2 days at +3° and then introduced into a mixture of ice/water and a 25% ammonia solution. The thus-precipitated product is worked up as set forth in Example A. After chromatography of the crude product on silica gel with acetone/hexane, 1.6 g. of 9-chloro-11β-fluoro-4-androstene-3,17-dione is isolated as an oil. UV: ε239 = 16,200 (methanol).

Workup

  1. additionAt -78°, a mixture of 15 ml

Sources & evidence

ORD record
ord-79b85f61a0a843e49616a848255b4132
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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