Reaction #1256711

Reaction equation

9

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

NaOAc

hydroxylamine hydrochloride

→

title compound

Yield 99.0%

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

Yield 99.0%

Solvents

MeOH

Conditions

Workup

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

Procedure

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