ChemicalBook CAS DataBase List 2-CHLOROLEPIDINE

2-CHLOROLEPIDINE synthesis

10synthesis methods

Product Name:2-CHLOROLEPIDINE
CAS Number:634-47-9
Molecular formula:C10H8ClN
Molecular Weight:177.63

4053-40-1

634-47-9

General method: 4-Methylquinoline-N-oxide (1.0 eq.) was dissolved in anhydrous dichloromethane (0.1 M) at 0 °C. Phosphorous trichloride (1.2 eq.) was added slowly with stirring, followed by the addition of N,N-dimethylformamide (0.5 eq.) dropwise under argon protection. The reaction mixture was gradually warmed to 25 °C with continuous stirring until the reaction was complete (monitored by TLC). After completion of the reaction, saturated aqueous sodium carbonate solution was slowly added and the pH was adjusted to 7~8. The aqueous phase was extracted with dichloromethane, the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to obtain the crude product. The crude product was purified by fast column chromatography using petroleum ether/ethyl acetate (80:1) as eluent to obtain 2-chloro-4-methylquinoline.

4053-40-1
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634-47-9
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Yield:634-47-9 81%

Reaction Conditions:

with trichlorophosphate in dichloromethane;N,N-dimethyl-formamide at 0 - 25;Inert atmosphere;regioselective reaction;

Steps:

General Procedure: chlorination of azine N-oxides

General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH₂Cl₂ (0.1M) at 0 °C is added POCl₃ (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7~8. The resulting mixture is separated and the aqueous phase is extracted with CH₂Cl₂ thoroughly. The organic phase is combined and washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (80:1) as eluent.

References:

Wang, Dong;Jia, Hailing;Wang, Wuchang;Wang, Zhe [Tetrahedron Letters,2014,vol. 55,# 51,p. 7130 - 7132] Location in patent:supporting information

607-66-9 Synthesis