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

HRID 2081995Notes

Reaction equation

HRID 2081995 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. NMR (CDCl3) δ 9.3-9.1 (br s, 1H, C2 pyridinium proton), 8.8-8.6 (br d, 1H, C6 pyridinium proton, 8.4-8.2 (br d, 1H, C4 pyridinium proton, 7.5-7.1 (m, 2-H, C5 pyridinium proton+C1 . estrone proton), 7.0-6.7 (m, 2H, C2,4 estrone protons), 3.2-1.3 (estrone skeletal protons, 15), 1.0-0.9 (s, 3H, C18 estrone protons). IR (KBr) 1750-1730 cm-1 (broad C=O stretching). 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; ##STR1561##

Workup

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

Sources & evidence

ORD record
ord-9b889b3ef557412aaa8771ac8d35072c
Source dataset
uspto-grants-1993_02
Patent number
US05187158

Reaction notes

Loading…