Nitric Acid → (Z)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile

HRID 42648

Reaktionsgleichung

Reaktionsgleichung von HRID 42648
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](/[C:12]2[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)\[C:10]#[N:11])=[CH:4][C:3]=1[O:22][CH3:23].[N+:24]([O-])([OH:26])=[O:25]>C(O)(=O)C>[OH:1][C:2]1[C:7]([N+:24]([O-:26])=[O:25])=[CH:6][C:5](/[CH:8]=[C:9](/[C:12]2[CH:13]=[N:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=2)\[C:10]#[N:11])=[CH:4][C:3]=1[O:22][CH3:23]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 68702729(Z)-3-(4-hydroxy-3-methoxyphenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile

Produkt 1

HCID 68704277(Z)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of (Z)-3-(4-hydroxy-3-methoxyphenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile (0.858 g, 2.68 mmol) in acetic acid (20 mL) was added 60% nitric acid (0.23 mL, 2.95 mmol) dropwise. The resulting mixture was allowed to stir at room temperature for thirty minutes then poured onto ice-water (100 mL). The yellow precipitate was filtered off, washed with water and dried. Recrystallisation from isopropanol afforded (Z)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile as a yellow solid, 0.597 g, (61%).

Aufarbeitung

  1. additionthen poured onto ice-water (100 mL)
  2. filtrationThe yellow precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customRecrystallisation from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-08a0a121d3834499a6944cdc1dae2b04
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536203B2

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