Phosphorus oxychloride → 4-Chloro-1,6-naphthyridine

HRID 503582ノート

反応式

HRID 503582 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[C:4](O)=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178516446HCID 178516446、化合物

生成物 1

HCID 217666944-Chloro-1,6-naphthyridine

実験手順

1,6-naphthyridin-4-ol (0.530 g, 3.63 mmol) was dissolved in phosphorus oxychloride (4.06 ml, 43.5 mmol) and heated at reflux for 14 h. Excess POCl3 was removed under reduced pressure and the mixture was azeotroped with toluene. The resultant gum was treated with sat. NaHCO3 until no gas was generated. The mixture was extracted with EtOAc, the combined extracts were washed with sodium bicarbonate and the solvent was removed under reduced pressure. The crude product was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-90% EtOAc/DCM) to afford 4-chloro-1,6-naphthyridine as a white solid.

後処理

  1. temperatureheated
  2. temperatureat reflux for 14 h
  3. customExcess POCl3 was removed under reduced pressure
  4. customthe mixture was azeotroped with toluene
  5. additionThe resultant gum was treated with sat. NaHCO3 until no gas
  6. extractionThe mixture was extracted with EtOAc
  7. washthe combined extracts were washed with sodium bicarbonate
  8. customthe solvent was removed under reduced pressure
  9. customThe crude product was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-90% EtOAc/DCM)

出典と根拠

ORDレコード
ord-459e2e0044c0453bb53d659e15108b44
出典データセット
uspto-grants-2010_08
特許番号
US07776857B2

反応ノート

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