反応 #1833213

反応方程式

Methyl 4-amino-3,6-dichloropicolinate

periodic acid

iodine

→

title compound

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

溶媒

methanol

反応条件

後処理

1. 1
   濃縮The reaction mixture was concentrated
2. 2
   workup.ADDITIONdiluted with diethyl ether
3. 3
   洗浄washed twice with saturated aqueous sodium bisulfate
4. 4
   抽出The aqueous layers were extracted once with diethyl ether
5. 5
   乾燥the combined organic layers were dried over anhydrous sodium sulfate
6. 6
   濃縮The product was concentrated
7. 7
   その他purified by flash chromatography (silica gel, 0-50% ethyl acetate/hexanes)

実験手順

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.

出典