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

HRID 2289512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2289512
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 rhe 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 and rhe residue
  3. dissolutionwas dissolved in ethyl acetate
  4. customchromatographed over silica gel (eluent: 90:10 v/v ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-50781e9ad5c14424aeeae9c75cffe3ff
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06093727

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