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ChemicalBook CAS DataBase List Methyl 5-broMo-2-chloro-1,6-dihydro-1-Methyl-6-oxopyridine-3-carboxylate
869357-63-1

Methyl 5-broMo-2-chloro-1,6-dihydro-1-Methyl-6-oxopyridine-3-carboxylate synthesis

3synthesis methods
methyl 2-chloro-1,6-dihydro-1-methyl-6-oxopyridine-3-carboxylate

853109-24-7

Methyl 5-broMo-2-chloro-1,6-dihydro-1-Methyl-6-oxopyridine-3-carboxylate

869357-63-1

General procedure for the synthesis of methyl 5-bromo-2-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate from methyl 2-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate: to methyl 2-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (0.100 g, 0.496 mmol) in dimethylformamide ( DMF, 5 mL) solution was added N-bromosuccinimide (NBS, 0.177 g, 0.992 mmol). The reaction mixture was stirred at room temperature in a nitrogen (N2) atmosphere for 4 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium bisulfite solution and subsequently diluted and layered with ethyl acetate (EtOAc) and water (H2O). The aqueous layer was back-extracted with ethyl acetate (2×). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give a yellow solid product in quantitative yield.

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Yield:869357-63-1 100%

Reaction Conditions:

with N-Bromosuccinimide in N,N-dimethyl-formamide at 20; for 4 h;

Steps:

13.C

To a solution of methyl 2-chloro-l-methyl-6-oxo-l,6- dihydropyridine-3-carboxylate (0.100 g, 0.496 mmol) in DMF (5 mL) was added N- bromosuccinimide (0.177 g, 0.992 mmol) and the reaction mixture was stirred for 4 hours at room temperature under N2. The reaction mixture was quenched with saturated sodium bisulfite and then diluted with EtOAc and H2O and the layers separated. The aqueous layer was back extracted with EtOAc (2x). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to yield a yellow solid in quantitative yield

References:

WO2007/44084,2007,A2 Location in patent:Page/Page column 77