تفاعل #48083

معادلة التفاعل

HCl

2-chloro-6-methyl-4-(trifluoromethyl)-pyridine

tetrabutylammonium permanganate

water

NaHSO3

→

gray liquid

المردود 67.0%

6-chloro-4-trifluoromethyl-pyridine-2-carboxylic acid

المردود 67.0%

المذيبات

pyridine

pyridine

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl acetate
2. 2
   غسيلThe combined organic layers were then washed with 1N HCl and brine
3. 3
   تجفيفdried (Na2SO4)
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe remaining residue was purified by chromatography (DCM/MeOH 100:0 to 90:10)

الإجراء التجريبي

To a solution of 300 mg of 2-chloro-6-methyl-4-(trifluoromethyl)-pyridine (1.49 mmol) in pyridine (5 ml) was added a solution of 1.61 g of tetrabutylammonium permanganate (4.46 mmol) in pyridine (4.5 ml) and the reaction mixture was stirred at 80° C. for 3 h. The reaction mixture was then poured into a mixture of water and ice and then NaHSO3 solution (40% in water) was added until the color turned light yellow. The mixture was then acidified by addition of 2N HCl and extracted with ethyl acetate. The combined organic layers were then washed with 1N HCl and brine, dried (Na2SO4), filtered and concentrated. The remaining residue was purified by chromatography (DCM/MeOH 100:0 to 90:10) to yield 224 mg (67%) of a gray liquid. MS (ISP) 224.3 (M−H)−.

المصدر