Isobutanol → 2-(5,6,7,8-Tetrahydroquinolin-3-yl)amino-2-imidazoline

HRID 361401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 361401
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1S(O)(=O)=O.[CH2:10](O)[CH:11]([CH3:13])[CH3:12].[C:15](O)(=O)/[CH:16]=[CH:17]/C(O)=O>C(O)C>[N:1]1[C:12]2[CH2:15][CH2:16][CH2:17][CH2:13][C:11]=2[CH:10]=[C:4]([NH:3][C:2]2[NH:1][CH2:5][CH2:4][N:3]=2)[CH:5]=1

Komponenten

5

Edukt 3

HCID 6560IsobutanolHCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acidHCID 444972Fumaric Acid

Produkt 1

HCID 234991692-(5,6,7,8-Tetrahydroquinolin-3-yl)amino-2-imidazolineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of the above solid (0.221 g, 1.49 mmole), 2-imidazoline-2-sulfonic acid (0.805 g, 5.4 mmole) and isobutyl alcohol (4 mL) was refluxed for 18 hours. The solvent was removed in vacuo and the residue was flash chromatographed over silica gel (eluent: 10:2:1 v/v/v ethyl acetate-methanol-triethylamine). The product was obtained in 100% yield (0.337 g) as a pale yellow solid. The above solid was treated in ethanol with 1.0 equivalent of fumaric acid to give a fumarate as a white solid (59% yield): mp 201°-203° C. Anal. Calcd. for C12H16N4.1.5C4H4O4.0.5H2O: C, 54.13; H, 5.76; N, 14.04. Found: C, 54.04; H, 5.96; N, 13.69.

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. customThe solvent was removed in vacuo
  3. customchromatographed over silica gel (eluent: 10:2:1 v/v/v ethyl acetate-methanol-triethylamine)
  4. customThe product was obtained in 100% yield (0.337 g) as a pale yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-c2596aef61f547bbb6404bb4e3aa411c
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866579

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