4-Nitrophenol → 2-[(4-Nitrophenoxy)methyl]quinoline

HRID 1452781

Reaktionsgleichung

Reaktionsgleichung von HRID 1452781
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1>CN(C=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]

Komponenten

5

Edukt 3

HCID 9804-NitrophenolHCID 203942-(Chloromethyl)quinolineHCID 24758Sodium hydride

Produkt 1

HCID 137703602-[(4-Nitrophenoxy)methyl]quinolineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

0.4 g (11 mmole) of 60% NaH is introduced into a flask containing 25 ml of anhydrous DMF under an argon atmosphere. A solution of 1.38 g (10 mmole) of 4-nitrophenol in 5 ml of anhydrous DMF is added dropwise, under agitation at 23° C. After 30 minutes a solution of 1.77 g (10 mmole) of 2-(chloromethyl)-quinoline in 5 ml of anhydrous DMF is added dropwise and agitation is continued for 15 hours while heating the mixture at 90° C. At the end of the reaction, the mixture is poured onto ice and an abundant precipitate forms. The suspension is filtered, rinsed twice with 25 ml of water followed by 20 ml of ethyl ether. A white solid is thus obtained with a yield of 75%. Melting point: 154-155° C.

Aufarbeitung

  1. customAt the end of the reaction
  2. additionthe mixture is poured onto ice
  3. filtrationThe suspension is filtered
  4. washrinsed twice with 25 ml of water
  5. customA white solid is thus obtained with a yield of 75%

Quellen und Nachweise

ORD-Eintrag
ord-7c5a8585840943639998021c9e2c21f8
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473779B2

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