Réaction #1256711

Équation de réaction

9

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

NaOAc

hydroxylamine hydrochloride

→

title compound

Rendement 99.0%

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

Rendement 99.0%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   AutreThe resulting solution was next partitioned between an aqueous 0.1 M NaOH solution (50 mL) and CH2Cl2 (50 mL×3)
2. 2
   AutreThe organic layer was separated
3. 3
   Séchagedried over anhydrous Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe crude product was next purified by flash chromatography on silica gel
7. 7
   Lavageeluting with ethyl acetate

Mode opératoire

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.

Source