反応 #1256711

反応方程式

9

4-(3,5-dimethylpyridin-4-yl)-N-(diphenylmethylene)-3,5-dimethyl-benzenamine

NaOAc

hydroxylamine hydrochloride

→

title compound

収率 99.0%

4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenylamine

収率 99.0%

溶媒

MeOH

反応条件

後処理

1. 1
   その他The resulting solution was next partitioned between an aqueous 0.1 M NaOH solution (50 mL) and CH2Cl2 (50 mL×3)
2. 2
   その他The organic layer was separated
3. 3
   乾燥dried over anhydrous Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The crude product was next purified by flash chromatography on silica gel
7. 7
   洗浄eluting with ethyl acetate

実験手順

To a solution of 9 (0.36 g, 0.93 mmol) in anhydrous MeOH (10 mL) at room temperature was added with stirring NaOAc (0. 197g, 2.40 mmol) and hydroxylamine hydrochloride (0.125 g, 1.80 mmol). The reaction mixture was then stirred at room temperature for 1.5 h. The resulting solution was next partitioned between an aqueous 0.1 M NaOH solution (50 mL) and CH2Cl2 (50 mL×3). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was next purified by flash chromatography on silica gel, eluting with ethyl acetate, to give 0.207 g (99.0%) of the title compound as yellow solid: mp 134-135° C.; 1H NMR (400 MHz, CD2Cl2): δ 8.311 (s, 2H), 6.482 (s, 2H), 1.903 (s, 6H), 1.769 (s, 6H); 13 C NMR (100 MHz, CD2Cl2): δ 149.130, 148.547, 146.482, 135.882, 132.333, 127.592, 114.635, 19.979, 16.876; MS(ESI): m/z 227.5 [(M+H)+, 100]; Anal. Calcd. for C15H18N2: C, 79.61; H, 8.02; N, 12.38. Found; C, 79.26; H, 7.91; N, 12.04.

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