ChemicalBook CAS DataBase List ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate

ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate synthesis

7synthesis methods

Product Name:ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate
CAS Number:127094-57-9
Molecular formula:C11H8Cl2N2O2
Molecular Weight:271.1

6-Bromo-4-hydroxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester

1184919-05-8
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ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate

127094-57-9
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$375.00/0.5 G

Yield:127094-57-9 44.5%

Reaction Conditions:

with dimethyl amine;trichlorophosphate for 3 h;Reflux;

Steps:

I.4 4. Preparation of ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate
4. Preparation of ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate ethyl 6-bromo-4-hydroxy-1,5-naphthyridine-3-carboxylate (49.8g, 0.168mmol) and N,N-dimethylamine(8mL) were added tophosphorus oxychloride(400mL). The mixture was heated to reflux for 3h. The reaction mixture was cooled. Phosphorus oxychloride was removed by evaporation under a reduced pressure. The resulting residual was poured into an ice-water mixture. The resulting mixture was adjusted with a sodium bicarbonate solution to pH≈8, and then extracted with dichlormethane. The organic phase was dried with anhydrous sodium sulfate, concentrated, and purified with a silica-gel column chromatography (petroleum ether:ethyl acetate=3:1) to produce 20.2g of the title compound as a pale-yellow solid in a yield of 44.5%.

References:

Xuanzhu Pharma Co., Ltd.;WU, Frank;ZHANG, Yan EP2719697, 2014, A1 Location in patent:Paragraph 0100

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13534-97-9 Synthesis