Phosphorus pentachloride → 3-Chloropyridine-2-carbonitrile

HRID 233481ノート

反応式

HRID 233481 の反応式
O[C:2]1[C:3]([C:8]([NH2:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12]>P(Cl)(Cl)(Cl)=O>[Cl:12][C:2]1[C:3]([C:8]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 24819Phosphorus pentachlorideHCID 702773-Hydroxypicolinamide

生成物 1

HCID 8182583-Chloropyridine-2-carbonitrile収率 14.9%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

To a solution of 3-hydroxypicolinamide (2.00 g, 14.5 mmol) in phosphorus oxychloride (10 mL) at room temperature was added phosphorus pentachloride (6.00 g, 28.8 mmol). The mixture was heated at reflux for 90 min, and the solvent was removed by distillation. The residue was poured into water, the aqueous solution was neutralized by addition of sodium bicarbonate, and was extracted with ethyl acetate. The organic phase was filtered through silica gel, the filtrate was concentrated, and the residue was subjected to flash chromatography on silica gel, affording 300 mg of 3-chloro-2-cyanopyridine. 1H NMR (CDCl3) δ7.50 (dd, 1, J=4.8, 8.4), 7.89 (dd, 1, J=l.6, 8.4), 8.63 (dd, 1, J=l.6, 4.8).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 min
  3. customthe solvent was removed by distillation
  4. additionThe residue was poured into water
  5. additionthe aqueous solution was neutralized by addition of sodium bicarbonate
  6. extractionwas extracted with ethyl acetate
  7. filtrationThe organic phase was filtered through silica gel
  8. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-1ee32c16c4734b3d888049e400d7701b
出典データセット
uspto-grants-1997_01
特許番号
US05593986

反応ノート

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