ChemicalBook >?? ???? >7-???-4-?????
7-???-4-?????
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7-???-4-????? ??
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- 150-152.5 °C
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- 366.8±27.0 °C(Predicted)
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- 1.363±0.06 g/cm3(Predicted)
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- under inert gas (nitrogen or Argon) at 2–8 °C
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- 7.49±0.50(Predicted)
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- CAS ??????
- 1198-40-9(CAS DataBase Reference)
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7-???-4-????? C??? ??, ??, ??
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7-Chloroquinolin-4-amine is an aminoquinoline that complexes ferriprotoporphyrin IX (Fe(III)PPIX) and inhibits its conversion to β-hematin (hemozoin).Synthesis Reference(s)
Journal of the American Chemical Society, 69, p. 704, 1947 DOI: 10.1021/ja01195a501Synthesis
4-amino-7-chloroquinoline is obtained byreacting 7-chloro-4-hydrazinoquinoline ,sodium borohydride with nickel (II) chloride hexahydrate in methanol.To a suspension of 7-chloro-4-hydrazinoquinoline (1.67 g, 8.6 mmol) and nickel (II) chloride hexahydrate (2.00 g, 8.6 mmol) in methanol (33 ml), sodium borohydride (0.98 g, 25.8 mmol) was added cautiously while stirring the reaction mixture vigorously at room temperature and left to react overnight. The reaction mixture was filtered through celite pad. Water was used to dilute the filtrate layer and then washed with ethyl acetate. The organic layer was dried with magnesium sulphate and concentrated in vacuo to give the title compound as a yellow powder (1.09 g, 72%): mp: 143 – 147 ℃ (Lit.: 147 – 148 ℃) ;vmax/cm-1 3337 s (N-H), 1642 m (C=N), 1609 m and 1575 m (C=N); δH (300 MHz; DMSO-d6) 8.28 (1H, d, J 5.3, C(2)H), 8.19 (1H, d, J 9.1, C(5)H), 7.76 (1H, d, J 1.6, C(8)H), 7.39 (1H, dd, J 9.1, 1.6, C(6)H), 7.03 (2H, s, NH2), 6.57 (1H, d, J 5.3, C(3)H); δC (75 MHz; DMSO-d6) 152.0 (Ar-C), 151.1 (C(2)H), 148.9 (Ar-C), 133.7 (Ar-C), 126.8 (C(8)H), 124.8 (C(5)H), 123.9 (C(6)H), 117.0 (Ar-C), 102.7 (C(3)H); m/z (-ES) 179 (100%, [M+H]- with 35Cl), 181 (35%, [M+H]- with 37Cl); found by +ES 179.0377, C9H8ClN2 ([M+H]+ with 35Cl), requires 179.0371, error 3.3 ppm.
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7-???-4-????? ?? ??:
7-CHLOROQUINOLINE
5-CHLOROQUINOLIN-8-AMINE
Hydroxychloroquine
Hydroxychloroquine sulfate
7-CHLORO-4-HYDRAZINOQUINOLINE
Amodiaquin dihydrochloride dihydrate
CHLOROQUINE
Chloroquine diphosphate
QUINACRINE MUSTARD DIHYDROCHLORIDE
1-GLYCERYL N-[7-CHLORO-4-QUINOLYL]ANTHRANILATE HYDROCHLORIDE
Mepacrine hydrochloride
6-CHLORO-9-[3-N-(2-CHLOROETHYL)ETHYLAMINO]PROPYLAMINO-2-METHOXYACRIDINE DIHYDROCHLORIDE
7-CHLORO-4-HYDRAZINO-2-METHYLQUINOLINE
6-CHLORO-9-[3-(2-CHLOROETHYLAMINO)PROPYLAMINO]-2-METHOXYACRIDINE DIHYDROCHLORIDE
2-(7-CHLOROQUINOLIN-4-YLAMINO)ETHANOL
7-CHLORO-2,8-DIMETHYL-4-HYDRAZINOQUINOLINE
BUTTPARK 51\09-71
ACRIDINE HOMODIMER