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ChemicalBook CAS DataBase List 8-CHLORO-[1,7]NAPHTHYRIDINE
13058-77-0

8-CHLORO-[1,7]NAPHTHYRIDINE synthesis

4synthesis methods
-

Yield: 62%

Reaction Conditions:

with trichlorophosphate at 100; for 16 h;

Steps:

10.3 Step 3 : 8-Chloro-l , 7-naphthyridine
A solution of 1, 7-naphthyridin-8-ol (2.0 g, 13.7 mmol) in P0C13 (20 mL) was heated at 100°C for 16 hours, and the product formation was confirmed by TLC. The reaction mixture was cooled to room temperature, and evaporated to dryness. Aq. NaHC03 solution (20 mL) was added thereto, and the mixture was extracted with ethyl acetate (3 x 25 mL) . The combined organic layers were washed with brine (25 mL) and dried over sodium sulfate. The organic layer was evaporated under vacuo, and the residue was purified by column chromatography using 2-5 % methanol in DCM as a mobile phase to give the title compound (1.4 g, 62 %) . MS(EI)m/z: 165.3 (M+l) ; XH NMR (400 MHz, , DMSO-d6) : δ 7.64 (d, J = 6.0 Hz, 1H) , 7.70 (dd, J= 4.0 & 8.4 Hz, 1H) , 8.22 (dd, J = 1.6 & 8.4 Hz, 1H) , 8.40 (d, J = 6.0 Hz, 1H) , 9.15 (dd, J = 1.6 & 4.0 Hz, 1H)

References:

TAKEDA PHARMACEUTICAL COMPANY LIMITED;BARAWKAR, Dinesh;DESHPANDE, Anil, M.;PATIL, Santosh;WAMAN, Yogesh;PANMAND, Anil;JADHAV, Dilip;KULKARNI, Bheemashankar WO2017/14323, 2017, A1 Location in patent:Paragraph 0280

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