Nitric Acid → 4-Nitroestrone

HRID 1003188

反応式

HRID 1003188 の反応式
[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]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 4763PhenobarbitalHCID 5870Estrone

生成物 1

HCID 2334974-Nitroestrone収率 13%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
120 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-26917a0d1732430e89cf51678fd6184c
出典データセット
uspto-grants-2000_04
特許番号
US06046186

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