1-Butanol → 4-(Pyridin-3-yl)pyridin-2-amine

HRID 40829

Reaktionsgleichung

Reaktionsgleichung von HRID 40829
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.[N+]([O-])(O)=O.[NH2:18][C:19]([NH2:21])=N.[OH-].[Na+].[CH2:24](O)CCC>>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[CH:4]=[CH:3][N:18]=[C:19]([NH2:21])[CH:24]=2)[CH:8]=1

Komponenten

5

Edukt 4

HCID 2631-ButanolHCID 10481Guanidine NitrateHCID 14798Sodium HydroxideHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

Produkt 1

HCID 167414844-(Pyridin-3-yl)pyridin-2-amineAusbeute 85 %

Versuchsvorschrift

3-(Dimethylamino)-1-(pyridine-3-yl)prop-2-en-1-one (15.4 g, 0.088 mol), guanidine nitrate (10.7 g, 0.088 mol), and sodium hydroxide (3.5 g, 0.088 mol) were dissolved in n-butanol (120 mL). The mixture was heated to reflux with stirring and maintained for 16 hours. The reaction mixture was then cooled to room temperature. The solid was collected and washed with water (400 mL). The desired product was dried under vacuum for three days and 12.7 g of yellow crystals of desired product was obtained (yield: 85%); 1H NMR (500 MHz, CDCl3) δ 5.15 (br., 2H), 7.09 (d, 1H), 7.44 (m, 1H), 8.33 (d, 1H), 8.42 (d, 1H), 8.73 (d, 1H), 9.22 (s, 1H). LC-MS (m/z) calculated, 172.2, found 173.2 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained for 16 hours
  4. customThe solid was collected
  5. washwashed with water (400 mL)
  6. dry with materialThe desired product was dried under vacuum for three days

Quellen und Nachweise

ORD-Eintrag
ord-c87ada3ed37b452fbec27d14d79e9694
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530492B2

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