반응 #1833213

반응 방정식

Methyl 4-amino-3,6-dichloropicolinate

periodic acid

iodine

→

title compound

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

용매

methanol

반응 조건

후처리

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

실험 절차

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.

출처