Reaktion #1833213

Reaktionsgleichung

Methyl 4-amino-3,6-dichloropicolinate

periodic acid

iodine

→

title compound

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

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle