Reaktion #62101

Reaktionsgleichung

2-[4-(4-Pyridin-4-yl-2H-pyrazol-3-yl)-phenoxymethyl}-quinoline

methyl hydrazine

sulfuric acid

→

title compound

Ausbeute 17.0%

2-[4-(2-Methyl-4-pyridin-4-yl-2H-pyrazol-3-yl)-phenoxymethyl]-quinoline

Ausbeute 17.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesolvent evaporated
2. 2
   SonstigeThe reaction mixture was partitioned between methylene chloride and saturated sodium bicarbonate
3. 3
   SonstigeThe layers were separated
4. 4
   Filtrationthe organic layer dried magnesium sulfate, filtered
5. 5
   Einengenconcentrated

Vorschrift

To a solution of 2-[4-(4-Pyridin-4-yl-2H-pyrazol-3-yl)-phenoxymethyl}-quinoline (1.72 g) in ethanol (20 ml) was added methyl hydrazine (3.5 ml, 1.5 eq.) and concentrated sulfuric acid (0.1 ml). The reaction mixture was stirred 1 h at ambient temperature and solvent evaporated. The reaction mixture was partitioned between methylene chloride and saturated sodium bicarbonate. The layers were separated and the organic layer dried magnesium sulfate, filtered and concentrated. Preparative HPLC chromatography provided the title compound (minor isomer) as a white solid (0.30 g, 17%). 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J=5.4 Hz, 2 H), 8.21 (d, J=8.7 Hz, 1 H), 7.80 (d, J=8.3 Hz, 1H), 7.77 (s, 1 H), 7.66 (m, 3 H), 7.53 (m, 1H), 7.19 (d, J=8.7 Hz, 2 H), 7.11 (d, J=8.7 Hz, 2H), 7.01 (d, J=6.2 Hz, 2H) 5.40 (s, 2H), 3.69 (s, 3H); MS: (M+H m/z=393.3).

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