ChemicalBook CAS DataBase List Methyl 4-chloro-6-methylnicotinate

Methyl 4-chloro-6-methylnicotinate synthesis

5synthesis methods

Product Name:Methyl 4-chloro-6-methylnicotinate
CAS Number:53277-47-7
Molecular formula:C8H8ClNO2
Molecular Weight:185.61

30529-70-5 Synthesis

30529-70-5
284 suppliers
$6.00/1g

74-88-4
341 suppliers
$15.00/10g

53277-47-7
83 suppliers
$20.00/250mg

Yield:53277-47-7 99%

Reaction Conditions:

with potassium carbonate in DMF (N,N-dimethyl-formamide); for 18 h;

Steps:

11; 17

The first step of Scheme 11: To a stirred solution of 2-chloro-6-methyl-nicotinic acid (13.6 g, 80 mmol) in DMF (118 mL) was added potassium carbonate (30 g, 219 mmol) and methyl iodide (23 mL, 366 mmol). After 18 hours, the reaction was diluted with ethyl acetate (300 mL) and washed with water (200 mL). The organic layer was dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure. The material was loaded on silica gel and filtered through a buchner funnel eluding with 1:1 ethyl acetate to yield 14.8 g (99%) of 2-chloro-6-methyl-nicotinic acid methyl ester as a light orange liquid. ¹H NMR (400 MHz, CHLOROFORM-D) δ ppm 2.59 (s, 3H) 3.94 (s, 3H) 7.16 (d, J=7.83 Hz, 1H) 8.09 (d, J=7.83 Hz, 1H).

References:

US2005/203081,2005,A1 Location in patent:Page/Page column 12; 30

67-56-1 Synthesis