Triethylamine → 3-Chloropyridine-2-carbonitrile

HRID 502598ノート

反応式

HRID 502598 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 8182583-Chloropyridine-2-carbonitrile収率 84.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d6467b72557b4382aff3956d0bcd526e
出典データセット
uspto-grants-2010_08
特許番号
US07776847B2

反応ノート

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