Réaction #1833213

Équation de réaction

Methyl 4-amino-3,6-dichloropicolinate

periodic acid

iodine

→

title compound

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

Solvants

methanol

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source