ChemicalBook CAS DataBase List ETHYL 6-CHLORO-2-METHYLPYRIDINE-3-CARBOXYLATE

ETHYL 6-CHLORO-2-METHYLPYRIDINE-3-CARBOXYLATE synthesis

9synthesis methods

Product Name:ETHYL 6-CHLORO-2-METHYLPYRIDINE-3-CARBOXYLATE
CAS Number:31163-12-9
Molecular formula:C9H10ClNO2
Molecular Weight:199.63

ETHYL 6-HYDROXY-2-METHYLPYRIDINE-3-CARBOXYLATE

3424-43-9
76 suppliers
$53.00/100mg

ETHYL 6-CHLORO-2-METHYLPYRIDINE-3-CARBOXYLATE

31163-12-9
46 suppliers
$45.00/1g

Yield: 89%

Reaction Conditions:

with trichlorophosphate in N,N-dimethyl-formamide at 120; for 2 h;Inert atmosphere;

Steps:

69 ethyl 6-chloro-2-methylnicotinate (4):
A solution of ethyl 6-hydroxy-2-methylnicotinate compound 3 (8.11 g, 44.6 mmol) andphosphorous oxychloride (20.0 g, 130 mmol) was stirred under nitrogen atmosphere at 120 °C for 2 hours. After cooling, the mixture was poured into ice water, basified with 8 M NaOH aqueoussolution, and extracted with EtOAc. The extract was washed with brine, dried over anhydrousNa2SO4 and concentrated under reduced pressure to obtain crude product, which was purified by silica gel column chromatography eluting with 30% EtOAc /PE to afford compound 4 (7.88 g,89%) as a colorless oil. LC-MS: m/z =200.0 [M+H]

References:

ABBVIE INC.;MICHAELIDES, Michael;HANSEN, Todd;DAI, Yujia;ZHU, Guidong;FREY, Robin;GONG, Jane;PENNING, Thomas;CURTIN, Michael;MCCLELLAN, William;CLARK, Richard;TORRENT, Maricel;MASTRACCHIO, Anthony;KESICKI, Edward A.;KLUGE, Arthur F.;PATANE, Michael A.;VAN DRIE, John H. Jr.;JI, Zhiqin;LAI, Chunqiu C.;WANG, Ce WO2016/44770, 2016, A1 Location in patent:Page/Page column 605

3424-43-9
76 suppliers
$53.00/100mg

31163-12-9
46 suppliers
$45.00/1g

References