Reaktion #1496033

Reaktionsgleichung

N-(2-methyl-5-nitrophenyl)-4-(pyridine-3-yl)pyridine-2-amine

hydrazine monohydrate

N-(2-methyl-5-nitrophenyl)-4-(pyridine-3-yl)pyridine-2-amine

→

6-Methyl-N-(4-(pyridine-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Ausbeute 56.4%

Lösungsmittel

methanol

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintained for 24 hours
2. 2
   TemperaturThe reaction mixture was cooled own to room temperature
3. 3
   SonstigeThe insoluble materials were removed by filtration
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe resulting residue was dissolved in ethyl acetate (150 mL)
6. 6
   Waschenwashed with water (150×2)
7. 7
   TrocknenThe organic phase was dried over anhydrous Na2SO4
8. 8
   SonstigeThe solvent was removed under reduced pressure
9. 9
   Sonstigethe resulting residue was purified by column chromatography (biotage: DMC/Methanol, 1-8%, 25 CV)
10. 10
    SonstigeThe product was obtained (1.57 g, yield: 56.4%) as a yellow solid and 0.53 g
11. 11
    Sonstigewas recovered

Vorschrift

N-(2-methyl-5-nitrophenyl)-4-(pyridine-3-yl)pyridine-2-amine (3.07 g, 10.0 mmol), hydrazine monohydrate (1.54 g of 65% solution in water, 20.0 mmol), FeCl3 (21 mg, 0.13 mmol), and activated carbon (0.2 g) were dissolved in a mixture of methanol (200 mL) and ethyl acetate (100 mL). The reaction mixture was heated to 80° C. with stirring and maintained for 24 hours. The reaction mixture was cooled own to room temperature. The insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (150 mL) and washed with water (150×2). The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography (biotage: DMC/Methanol, 1-8%, 25 CV). The product was obtained (1.57 g, yield: 56.4%) as a yellow solid and 0.53 g starting material of N-(2-methyl-5-nitrophenyl)-4-(pyridine-3-yl)pyridine-2-amine was recovered; 1H NMR (500 MHz, CDCl3) δ 2.28 (s, 3H), 3.68 (s, 2H), 6.45 (d, 1H), 6.95 (s, 1H), 7.02 (d, 1H), 7.18 (d, 1H), 7.45 (m, 1H), 7.35 (d, 1H), 7.65 (s, 1H), 8.37 (d, 1H), 8.52 (d, 1H), 8.74 (d, 1H), 9.28 (s, 1H). LC-MS (m/z) calculated, 277.3. found, 278.2 [M+H]+.

Quelle