Ammonia → HCID 13714630, compound

HRID 845215Notes

Reaction equation

HRID 845215 reaction equation
[NH2:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][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].N.[Li]>C(OCC)C>[NH2:1][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

5

Reactant 3

HCID 222AmmoniaHCID 3028194LithiumHCID 13714626HCID 13714626, compound

Product 1

HCID 13714630HCID 13714630, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 0.45 g of 4-aminoandrost-4,6-dien-3,17-dione in 20 ml of diethyl ether and 40 ml of liquid ammonia are added 0.28 g of lithium metal at small portions. The resulting blue reaction mixture is stirred for additional 30 minutes, quenched with absolute ethanol till the blue colour fades and allowed to reach the room temperature. The resulting residue is taken up with water, extracted with diethyl ether and purified as described in example 10. There are obtained 0.280 g of the title compound, m.p. 185°-187° C.

Workup

  1. customquenched with absolute ethanol till the blue colour fades
  2. customthe room temperature
  3. extractionextracted with diethyl ether
  4. custompurified

Sources & evidence

ORD record
ord-b65d976cd3a5472c9ffd913e5f2f0c52
Source dataset
uspto-grants-1988_07
Patent number
US04757061

Reaction notes

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