Реакция #1833213

Уравнение реакции

Methyl 4-amino-3,6-dichloropicolinate

periodic acid

iodine

→

title compound

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

Растворители

methanol

Условия реакции

Обработка

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

Методика

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.

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