Phosphorus oxychloride → 2-Chloro-4-cyanopyridine

반응식

[C:1]([C:3]1[CH:8]=[CH:7][N+:6]([O-])=[CH:5][CH:4]=1)#[N:2].P(Cl)(Cl)([Cl:12])=O>>[Cl:12][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][N:6]=1)[C:1]#[N:2]

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 846844-Pyridinecarbonitrile, 1-oxide

생성물 1

HCID 5686382-Chloro-4-cyanopyridine

반응 조건

온도: 110 °C

실험 절차

4-cyanopyridine-N-oxide (10.0 g) was added to phosphorus oxychloride (85 mL) and heated to 110° C. for 2.5 h. The mixture was cooled to room temperature and the excess phosphorus oxychloride removed under reduced pressure. The residue was dissolved in water and made basic with concentrated ammonia. The product was extracted into methylene chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using methylene chloride as eluent to give 7.19 g of the title compound: 1H NMR (CDCl3) δ 7.48, 7.6, 8.6.

후처리

temperatureThe mixture was cooled to room temperature
customthe excess phosphorus oxychloride removed under reduced pressure
dissolutionThe residue was dissolved in water
extractionThe product was extracted into methylene chloride
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록: ord-4fd89648bc414c0eafc7ff0e3e137c9e
출처 데이터셋: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07727997B2

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