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ChemicalBook CAS DataBase List Methyl 4,6-dichloronicotinate
65973-52-6

Methyl 4,6-dichloronicotinate synthesis

5synthesis methods
-

Yield:65973-52-6 97.2%

Reaction Conditions:

with triethylamine;trichlorophosphate at 0 - 120; for 2 h;

Steps:

1; 8 4,6-Dichloro-nicotinic acid methyl ester

4,6-Dihydroxy-nicotinic acid methyl ester (3.9 g, 23 mmol) (from Example 7 supra) was added to POCl3 (20 mL) at 0° C., then Et3N (5 mL) was added to the mixture slowly. After addition, the mixture was heated at 120° C. for 2 hours, then allowed to cool to 0° C. The reaction solution was poured slowly and portion-wise into ice-water (100 mL). Solid K2CO3 was added to adjust pH to 8. The resulting precipitate was collected by filtration. The solid was dissolved in ethyl acetate (50 mL), dried over anhydrous Na2SO4, filtered and concentrated to afford 4,6-dichloro-nicotinic acid methyl ester. (Yield 4.6 g, 97.2%). 1H NMR (301 MHz, CDCl3) δ 8.85 (s, 1H), 7.47 (s, 1H), 3.97 (s, 3H). LC-MS: [M+H]+ 205.9.

References:

US2012/184562,2012,A1 Location in patent:Page/Page column 6; 17

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