4-Nitroaniline → 2-Methyl-6-nitroquinoline

HRID 641805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641805
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:11](=O)/[CH:12]=[CH:13]/[CH3:14].[OH-].[K+]>Cl.C1(C)C=CC=CC=1>[CH3:14][C:13]1[CH:12]=[CH:11][C:9]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=2)[N:8]=1

Komponenten

6

Edukt 3

HCID 74754-NitroanilineHCID 14797Potassium HydroxideHCID 447466Crotonaldehyde

Produkt 1

HCID 691722-Methyl-6-nitroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Nitroaniline (6 g, 38 mmol) was dissolved in HCl (6N, 200 mL), the mixture was heated at 100° C. A solution of (E)-but-2-enal (7.2 mL, 76 mmol) in toluene (60 mL) was added dropwise, and the reaction was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and basified with aqueous KOH until pH=12. The mixture was extracted with EtOAc and the organic layer was washed with brine and dried over anhydrous Na2SO4. 2-Methyl-6-nitroquinoline was obtained after purification by column chromatography (hexane: EtOAc=20:1) (5.8 g, 81.2%). MS [M++1]=189, LC-MS: tR=1.64 min.

Aufarbeitung

  1. temperaturethe reaction was heated at 100° C. overnight
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-bf73c8ce90324ce880f8a88a1f1de6eb
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696227B2

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