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Hydrochloric Acid → 2-(p-Cyanophenyl)-5-octylpyridine

HRID 3933
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 3933
[CH3:1][N:2]1CCCC1=O.Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:17][N:16]=2)=[CH:11][CH:10]=1.[Cu]C#N.Cl>[Fe](Cl)Cl.O>[C:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:17][N:16]=2)=[CH:11][CH:10]=1)#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 135862762-(p-Bromophenyl)-5-octylpyridineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 135862772-(p-Cyanophenyl)-5-octylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24458
Ferrous Chloride
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

94 ml of N-methylpyrrolidone was added to the 47.6 g (0.138 mol) of the 2-(p-bromophenyl)-5-octylpyridine. Then 19.3 g (0.216 mol) of copper (I) cyanide was added and the solution was refluxed for 2 hours. A mixture of 69 g of iron (II) chloride, 13.8 ml of concentrated hydrochloric acid and 69 ml of water was added to the mixture solution and the organic layer was extracted with chloroform. The extract was washed with a 10% aqueous solution of potassium hydroxide and then three times with water. Chloroform was removed by distillation. The residue was distilled under reduced pressure (210° to 220° C./2 mmHg) and recrystallized from methanol to obtain 33 g (0.1113 mol) of 2-(p-cyanophenyl)-5-octylpyridine.

Aufarbeitung

  1. temperaturethe solution was refluxed for 2 hours
  2. additionwas added to the mixture solution
  3. extractionthe organic layer was extracted with chloroform
  4. washThe extract was washed with a 10% aqueous solution of potassium hydroxide
  5. customChloroform was removed by distillation
  6. distillationThe residue was distilled under reduced pressure (210° to 220° C./2 mmHg)
  7. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-3e38851339f345daa2b27e8a83160009
Quelldatensatz
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04723018

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