تفاعل #1833213

معادلة التفاعل

Methyl 4-amino-3,6-dichloropicolinate

periodic acid

iodine

→

title compound

Methyl 4-amino-3,6-dichloro-5-iodopicolinate

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture was concentrated
2. 2
   workup.ADDITIONdiluted with diethyl ether
3. 3
   غسيلwashed twice with saturated aqueous sodium bisulfate
4. 4
   استخلاصThe aqueous layers were extracted once with diethyl ether
5. 5
   تجفيفthe combined organic layers were dried over anhydrous sodium sulfate
6. 6
   تركيزThe product was concentrated
7. 7
   أخرىpurified by flash chromatography (silica gel, 0-50% ethyl acetate/hexanes)

الإجراء التجريبي

Methyl 4-amino-3,6-dichloropicolinate (10.0 g, 45.2 millimoles (mmol)), periodic acid (3.93 g, 17.2 mmol), and iodine (11.44 g, 45.1 mmol) were dissolved in methanol (30 mL) and stirred at reflux at 60° C. for 27 h. The reaction mixture was concentrated, diluted with diethyl ether, and washed twice with saturated aqueous sodium bisulfate. The aqueous layers were extracted once with diethyl ether, and the combined organic layers were dried over anhydrous sodium sulfate. The product was concentrated and purified by flash chromatography (silica gel, 0-50% ethyl acetate/hexanes) to provide the title compound as a pale yellow solid (12.44 g, 79%): mp 130.0-131.5° C.; 1H NMR (400 MHz, CDCl3) δ 5.56 (s, 2H), 3.97 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 163.80, 153.00, 152.75, 145.63, 112.12, 83.91, 53.21; EIMS m/z 346.

المصدر