O-Toluidine → 1-Tolyl-3-pyrroline

HRID 366870

Reaktionsgleichung

Reaktionsgleichung von HRID 366870
[CH3:1]/[CH:2]=[CH:3]\[CH3:4].[NH2:5][C:6]1[C:7]([CH3:12])=[CH:8][CH:9]=[CH:10][CH:11]=1>C1(C)C=CC=CC=1>[C:7]1([CH3:12])[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N:5]1[CH2:4][CH:3]=[CH:2][CH2:1]1

Komponenten

4

Edukt 2

HCID 7242O-ToluidineHCID 5287573cis-2-BUTENE

Produkt 1

HCID 158773171-Tolyl-3-pyrrolineAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 60.0 g of the cis-2-butene derivative solution prepared in Example 1 and 250 g of toluene in a round flask reactor, 171.7 g (1.6 mol) of toluidine was added dropwise with stirring for 30 min. at 50° C. After 2 hours of stirring, the crystallized solid was removed by filtration; 42.0 g of 35% HCl (aq) was added to the filtrate, and then excess benzylamine hydrochloride was removed by filtration or extraction. After the solvent was evaporated under reduced pressure, 56.8 g of 1-tolyl-3-pyrroline (yield 89.2%) was obtained.

Aufarbeitung

  1. stirringAfter 2 hours of stirring
  2. customthe crystallized solid was removed by filtration
  3. addition42.0 g of 35% HCl (aq) was added to the filtrate
  4. customexcess benzylamine hydrochloride was removed by filtration or extraction
  5. customAfter the solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f5b78b3fc8784131b379d94e83cdaf85
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130338

Verknüpfte Notizen

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