2,4,6-Trimethylpyridine → 4,4-Dimethyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

HRID 12382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12382
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].N1C(C)=CC(C)=CC=1C>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 79532,4,6-TrimethylpyridineHCID 738951-Fluoro-2-nitrobenzeneHCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 574233104,4-Dimethyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
250 °C

Versuchsvorschrift

1b (0.762 g, 4.73 mmol), ortho-fluoronitrobenzene (0.88 g, 5.67 mmol, 1.19 eq), and 2,4,6-collidine (0.66 mL, 1.05 eq) were pre-stirred 40s in a conical microwave container. It was then heated with stirring at a Personal Chemistry Microwave reactor with normal absorption at 250° C. for 1 h. The crude mixture was dissolved in CHCl3, and was purified by flash chromatography (hexanes/EtOAc) to give 0.66 g of crude 1c. LC-MS ESI 283 (M+H).

Aufarbeitung

  1. temperatureIt was then heated
  2. customwas purified by flash chromatography (hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6f4b0b70237f463091d7218d522edefa
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728008B2

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