Ammonia → 3-nitro-5,6,7,8-tetrahydroquinoline

HRID 1597354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1597354
C[N:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[C:3]1=O.[C:15]1(=O)[CH2:20]CC[CH2:17][CH2:16]1.N>CO>[N+:8]([C:6]1[CH:7]=[N:2][C:3]2[CH2:20][CH2:15][CH2:16][CH2:17][C:4]=2[CH:5]=1)([O-:10])=[O:9]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 7967CyclohexanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Produkt 1

HCID 110303733-nitro-5,6,7,8-tetrahydroquinolineAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-methyl-3,5-dinitro-2-pyridone (2.4 g, 0.012 mole), cyclohexanone (1.18 g, 0.012 mole) and ammonia solution (2.0M, 120 mL) in methanol was refluxed overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The soluble portion was flash chromatographed over silica gel (eluent: 90:10 v/v ethyl acetate-hexane) to give a yellow solid (2.02 g, 94% yield).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customchromatographed over silica gel (eluent: 90:10 v/v ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fdc1b675e618444bbdd94a55b73448ae
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294566B1

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