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[ CAS No. 724787-12-6 ] {[proInfo.proName]}

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Chemical Structure| 724787-12-6
Chemical Structure| 724787-12-6
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Product Details of [ 724787-12-6 ]

CAS No. :724787-12-6 MDL No. :MFCD16038309
Formula : C9H7ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 210.62 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 724787-12-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 724787-12-6 ]

[ 724787-12-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 23443-25-6 ]
  • [ 724787-12-6 ]
YieldReaction ConditionsOperation in experiment
80% With N-chloro-succinimide In acetic acid at 35℃; for 24h; 1.a A solution of 6-(methyloxy)-l,5-naphthyridin-4-ol (6-methoxy-lH- [l,5]naphthyridin-4-one, for a synthesis see WO2002096907 Example 1) (50 g; 0.2841 mol) in glacial acetic acid (750 niL) was treated with N-chlorosuccinimide (42.5 g; 0.3185 mol) and the mixture was heated under argon at 350C for 24 hours. It was cooled and the precipitated solid filtered off and washed with a little cold acetic acid, then ether and finally hexane. It was dried at 5O0C overnight in vacuo to give an off-white solid 48g (80%). LC/MS (+ve ion electrospray): m/z 209/211 (M+η)+
43% With N-chloro-succinimide; acetic acid at 30℃; for 16h; 3-chloro-6-methoxy-l,5-naphthyridin-4-ol To a mixture of 6-Methoxy-[1,5]naphthyridin-4-ol (19.4 g, 110.23 mmol) in acetic acid (330 mL)N-chlorosuccinimide (16.87 g, 126.76 mmol) was added, and the reaction solution was stirred at 30 °C for 16 h. After the reaction solution was cooled to room temperature, and a large amount of solid was precipitated and filtered. The filter cake was washed with diethyl ether and n-heptane, and dried to obtain an off-white solid (10 g, yield 43%). MS (ESI): m/z = 211 [M+H]+.
With N-chloro-succinimide In acetic acid at 65℃; for 1.5h; 46 4-Hydroxy-6-methoxy-l,5-naphthyridine (10.4g) and N-chlorosuccinimide (8.7g) were combined and heated at 65 °C in acetic acid (12OmL) for 1.5 hours. The mixture was cooled to room temperature, filtered, washed with water, saturated sodium bicarbonate solution, then with water again, and dried in vacuo to give product 3-chloro-4-hydroxy-6-methoxy-l,5-naphthyridine (12g).
With N-chloro-succinimide; acetic acid at 35℃; 25a 25a) 3-Chloro-6-methoxy-[1,5]-naphthyridin-4-ol6-Methoxy-[1,5]-naphthyridin-4-ol (la) (12 g) was suspended inacetic acid (200 ml) and warmed until all had dissolved, thenNCS (10 g) was added and the mixture stirred at 35°C over night.The mixture was cooled, the solid collected by filtration,washed with acetic acid and dried under vacuum to give thedesired product (13.1 g).XH NMR (300 MHz, d6-DMSO) : 8: 12.30 (bs, 1H) , 8.40 (s, 1H) , 7.98(d, 1H), 7.20 (d, 1H), 3.95 (s, 3H)
With N-chloro-succinimide In acetic acid at 35℃; for 18h; 4.a 6-Methoxy-[1 ,5]naphthyridin-4-ol (12 g) in acetic acid (200 mL) was sonicated and warmed until all had dissolved, and then it was treated with N-chlorosuccinimide (10.01 g) and the mixture was heated at 350C for 18 hr, cooled, and the solid collected and washed with acetic acid and dried in vacuo at 4O0C overnight, to give a white solid (9.5 g); MS (ES) m/z211/213 (M + H)+.
55.4 g With N-chloro-succinimide; acetic acid at 35 - 40℃; for 4h; Step 3To a solution of M.2 (50.0 g) in acetic acid (heating was needed to dissolve) was added N-chlorosuccinimide (41.7 g), the mixture was stirred at 35-40 °C for 4 hours. The resulting precipitates were collected by filtration. A suspension of the crude product in water was stirred at 80 °C for 1 hour. The precipitates were collected by filtration and washed with water to give M.3 (55.4 g).1H NMR (DMSO-dg): δ 4.07 (s, 3H), 7.47 (d, J= 9.2 Hz, 1H), 8.45 (d, J= 9.2 Hz, 1H), 8.65 (d, J= 2.4 Hz, 1H), 9.08 (s, 1H).
With N-chloro-succinimide; acetic acid at 60℃; for 3h; Inert atmosphere; 2.1 Stepl: 3-Chloro-6-methoxy-l,5-naphthyridin-4-ol (Xlla) To a stirred solution of 6-methoxy-l,5-naphthyridin-4-ol (10.0 g, 56.76 mmol) in glacial acetic acid (150 mL) at room temperature under nitrogen atmosphere was added N- chlorosuccinimide (8.48 g, 63.57 mmol). The reaction mixture was heated to 60 °C and stirred for 3 hour. After that, the reaction mixture was cold to room temperature and solid precipitated was filtered, washed with n-hexane and dried under vacuo to get compound Xlla as a white solid, which was used as such for the next step without any further purification. Yield: 10.0 g (crude), 85.03 %.LC_MS Calc for C9H7CIN2O2, 210.62; Obs: 211.0 [M++H]; -NMII (300 MHz, DMSO- d6): d 8.40 (s, 1H) 7.99 (d, J = 11.60 Hz, 1H), 7.20 (d, J = 12.0 Hz, 1H), 3.95 (s, 3H), 3.33 (brs, 1H).

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