ChemicalBook CAS DataBase List 2,9-Dichloro-1,10-phenanthroline

2,9-Dichloro-1,10-phenanthroline synthesis

9synthesis methods

Product Name:2,9-Dichloro-1,10-phenanthroline
CAS Number:29176-55-4
Molecular formula:C12H6Cl2N2
Molecular Weight:249.1

9-Chloro-1-methyl-1,10-phenanthrolin-2(1H)-one

29176-54-3
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29176-55-4
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Yield:29176-55-4 94%

Reaction Conditions:

Stage #1:9-chloro-1-methyl-1,10-phenanthroline-2(1H)-one with phosphorus pentachloride;trichlorophosphateInert atmosphere;cooling with ice;Reflux;
Stage #2: with ammonia in waterAlkaline conditions;

Steps:

6
Reference Example 62,9-Dichloro-1,10-phenanthroline (6) [0125] [Chem. 23] [0126] Under a stream of argon, to compound (5) (4.26 g; 17.4 mmol), phosphorus oxychloride (39 mL) and phosphorus pentachloride (4.48 g; 21.8 mmol) were added in an ice bath. The resulting reaction mixture was stirred and refluxed for 7 hours, and then evaporated under reduced pressure to remove phosphorus oxychloride. To the resulting residue, ice water and concentrated aqueous ammonia were added and the resulting reaction mixture was made alkaline. The solids which precipitated out were separated by filtration and washed with water, and then dried under reduced pressure to give 4.06 g (yield: 94%) of the title compound (6). [0127] ¹H NMR (DMSO-d₆) d: 7.90 (d, J = 8.5 Hz, 1 H), 8.12 (s, 2 H), 8.63 (d, J = 8.5 Hz, 1 H)HPLC mobile phase: 20-90% acetonitrile - water (0.1% trifluoroacetic acid) Peak retention time: 13.2 minutes

References:

Eisai R&D Management Co., Ltd.;SANKO JUNYAKU CO., LTD.;HOSHINO, Mikio;YANO, Toshisada WO2011/30566, 2011, A1 Location in patent:Page/Page column 24-25

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