Triethylamine → 3-Chloropyridine-2-carbonitrile

HRID 502598

반응식

HRID 502598 반응식
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.C[Si](C[C:14]#[N:15])(C)C.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[C:3]([C:14]#[N:15])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 87557(Trimethylsilyl)acetonitrileHCID 123133Pyridine, 3-chloro-, 1-oxide

생성물 1

HCID 8182583-Chloropyridine-2-carbonitrile수율 84.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-chloropyridine-N-oxide (2.12 g, 16.30 mmol), trimethylsilyl(acetonitrile) (3.25 g, 32.80 mmol), triethylamine (3.30 g, 32.60 mmol) and acetonitrile (10 mL) was heated at reflux for 6 h. After concentration under reduced pressure, the resulting residue was basified with aqueous sodium carbonate (3N) and extracted with methylene chloride. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 3-chloropicolinonitrile (1.90 g). The crude product was carried forward without further purification. MW=139 confirmed by LC-MS, tr=2.33 min (Method E) MH+=140.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. concentrationAfter concentration under reduced pressure
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d6467b72557b4382aff3956d0bcd526e
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776847B2

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