反応 #2333

反応方程式

4-chloropyridine hydrochloride

4-methoxyaniline

→

4-(4-pyridylamino)-methoxybenzene

溶媒

dichloromethane

反応条件

後処理

1. 1
   温度After cooling the residue
2. 2
   抽出the solution extracted with water (2×100 ml)
3. 3
   workup.ADDITIONThe aqueous extracts were treated with sodium hydroxide solution
4. 4
   抽出extracted with ethyl acetate (4×100 ml)
5. 5
   洗浄The combined organic extracts were washed with water, and saturated sodium chloride solution
6. 6
   その他dried
7. 7
   その他the solvent evaporated
8. 8
   その他Purification by flash chromatography on silica
9. 9
   洗浄eluting with 10% v/v methanol/dichloromethane

実験手順

A stirred mixture of 4-chloropyridine hydrochloride (2 g) and 4-methoxyaniline (4.9 g) was heated at 140° C. for 5 hours. After cooling the residue was dissolved in dichloromethane (250 ml), the solution extracted with water (2×100 ml). The aqueous extracts were treated with sodium hydroxide solution and then extracted with ethyl acetate (4×100 ml). The combined organic extracts were washed with water, and saturated sodium chloride solution, then dried and the solvent evaporated. Purification by flash chromatography on silica, eluting with 10% v/v methanol/dichloromethane gave 4-(4-pyridylamino)-methoxybenzene, 2 g, as a fawn solid: m.p. 159°-160° C.; NMR (d6DMSO) δ8.47 (1H, s), 8.09 (2H, d), 7.10 (2H, d), 6.92 (2H, d), 6.70 (2H, dd), 3.73 (3H, s); m/e 201 (M+H)+ ; calculated for C12H12 N2O3 : C, 72.0; H, 6.0; N, 14.0. found: C, 71.4; H, 6.1; N, 13.8%.

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