Estrone → 3-Nicotinoyloxyestra-1,3,5(10)-trien-17-one

HRID 2290513Notes

Reaction equation

HRID 2290513 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH3:11][C@@:12]12[C:28](=[O:29])[CH2:27][CH2:26][C@H:25]1[C@H:24]1[C@@H:15]([C:16]3[CH:17]=[CH:18][C:19]([OH:30])=[CH:20][C:21]=3[CH2:22][CH2:23]1)[CH2:14][CH2:13]2>N1C=CC=CC=1>[C:2]([O:30][C:19]1[CH:18]=[CH:17][C:16]2[C@@H:15]3[C@H:24]([C@H:25]4[C@@:12]([CH2:13][CH2:14]3)([CH3:11])[C:28](=[O:29])[CH2:27][CH2:26]4)[CH2:23][CH2:22][C:21]=2[CH:20]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 5870EstroneHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 137310683-Nicotinoyloxyestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To nicotinoyl chloride hydrochloride (2.65 g, 0.015 mol) in pyridine (20 ml) at 0° C. was added estrone (2 g, 0.0074 mol). The mixture was refluxed for one hour and then poured over 100 ml of ice cold water, filtered, and dried over P2O5 under vacuum. Yield 72% (2.0076 g), m.p. 207°-210° C. Anal. calculated for C24H25NO3 ; C, 76.76; H, 6.72; N, 3.73. Found: C, 76.37; H, 6.96; N, 3.67. The product is further characterized by the structural formula: ##STR85##

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationfiltered
  3. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-fdd553e54824409bac25a33661d9ce74
Source dataset
uspto-grants-1986_10
Patent number
US04617298

Reaction notes

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