Phosphorus oxychloride → 2-(2-Chloropyridin-3-yl)acetonitrile

HRID 751351ノート

反応式

HRID 751351 の反応式
[CH:1]1[CH:6]=[N+:5]([O-])[CH:4]=[C:3]([CH2:8][C:9]#[N:10])[CH:2]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:4]1[C:3]([CH2:8][C:9]#[N:10])=[CH:2][CH:1]=[CH:6][N:5]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 2431673-(Cyanomethyl)pyridin-1-ium-1-olate

生成物 1

HCID 147395432-(2-Chloropyridin-3-yl)acetonitrile収率 42.9%

反応条件

温度
5 °C

実験手順

(1-oxypyridin-3-yl)acetonitrile (7.5 g, 35.9 mmol) is carefully added to vigorously stirred phosphorous oxychloride (100 mL). The mixture is slowly heated to 80° C. (in 5° C. increments) over 1.5 hr. (CAUTION. If heating is too quick, violent decomposition occurs at ca 70° C.) All the solids dissolved. The reaction is heated at reflux for 3 hr. The excess phosphorous oxychloride is removed and the residue is cautiously treated with cold water. Saturated sodium bicarbonate is added to make the mixture basic, then it is extracted with ethyl acetate (3×). The combined extract is washed with brine, dried, filtered and concentrated. The residue is purified by chromatography eluting with pentane-10 to 100% ether. The second compound off the column is the desired (2-chloropyridin-3-yl)acetonitrile (2.35 g, 42.9% yield) a light brown solid.

後処理

  1. temperatureIf heating
  2. customoccurs at ca 70° C.
  3. dissolutiondissolved
  4. temperatureThe reaction is heated
  5. temperatureat reflux for 3 hr
  6. customThe excess phosphorous oxychloride is removed
  7. additionthe residue is cautiously treated with cold water
  8. additionSaturated sodium bicarbonate is added
  9. extractionit is extracted with ethyl acetate (3×)
  10. extractionThe combined extract
  11. washis washed with brine
  12. customdried
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe residue is purified by chromatography
  16. washeluting with pentane-10 to 100% ether

出典と根拠

ORDレコード
ord-a60c00aa524246eb92f144e60a468ac9
出典データセット
uspto-grants-2008_07
特許番号
US07405300B2

反応ノート

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