1-Iodopropane → 4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propylpyridinium iodide

HRID 419521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419521
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[I:19][CH2:20][CH2:21][CH3:22]>CC(=O)C(C)(C)C.CC(C)=O>[I-:19].[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][N+:16]([CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=1

Komponenten

5

Edukt 2

HCID 336431-IodopropaneHCID 594526494-[2-Methyl-5-(methyloxy)-4-nitrophenyl]pyridine

Produkt 1

HCID 666497594-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propylpyridinium iodideAusbeute 535,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6416PinacoloneLösungsmittel

Reaktionsbedingungen

Temperatur
102 °C

Versuchsvorschrift

To 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]pyridine (750 mg, 3.07 mmol) in 15 mL of pinacolone was added, 1-iodopropane (2.1 g, 2.66 mmol). The mixture was heated to 102° C. for 24 h. The mixture was cooled and diluted with acetone. The resulting slurry was filtered and washed with acetone. The product was dried under vacuum to give the title compound of step B (1.1 g, 14.24 mmol, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.19 (d, J=6.78 Hz, 2H), 8.30 (d, J=6.59 Hz, 2H), 7.94 (s, 1H), 7.37 (s, 1H), 4.61 (t, J=7.23 Hz, 2H), 3.93 (s, 3H), 2.26 (s, 3H), 1.92-2.02 (m, 2H), 0.92 (t, J=7.42 Hz, 3H).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationThe resulting slurry was filtered
  3. washwashed with acetone
  4. customThe product was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0bba2445645f4b5796e7665ba3fbb82c
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

Notizen zur Reaktion

Wird geladen…