Nitric Acid → 4-Nitroestrone

HRID 1003188

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HRID 1003188 반응식
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[N+:21]([O-])([OH:23])=[O:22].CCC1(C2C=CC=CC=2)C(=O)NC(=O)NC1=O>C(O)(=O)C>[OH:20][C:9]1[CH:8]=[CH:7][C:6]2[C@@H:5]3[C@H:14]([C@H:15]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[C:10]=1[N+:21]([O-:23])=[O:22]

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 4763PhenobarbitalHCID 5870Estrone

생성물 1

HCID 2334974-Nitroestrone수율 13%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
120 °C

실험 절차

To a suspension of estrone (11, 8.11 g, 30 mmol) in acetic acid (250 mL) was heated to 120° C. and cooled to 50° C. To the reaction mixture was added 70% nitric acid (2.27 mL, 36 nunol, in an acetic acid (8.0 mL) solution) at 50° C., and stirred for 20 h at room temperature. The precipitate was filtered and washed with acetic acid, H2O, Et2O to afford 1.18 g of 76a (13% yield) mp: >250° C. To the filtrate was added H2O; it was then extracted with Et2O. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (2:1, v/v) to afford 3.25 g of 76b (34% yield) mp: 178-180° C.

후처리

  1. temperaturecooled to 50° C
  2. filtrationThe precipitate was filtered
  3. washwashed with acetic acid, H2O, Et2O

출처 및 근거

ORD 기록
ord-26917a0d1732430e89cf51678fd6184c
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046186

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