Phosphorus oxychloride → 4-Chloro-1,5-naphthyridine

HRID 513749

反応式

HRID 513749 の反応式
O=P(Cl)(Cl)[Cl:3].[N+:6]1([O-])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1>>[Cl:3][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][N:11]=2)[N:6]=[CH:7][CH:8]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 3392321-Oxo-1lambda~5~-1,5-naphthyridine

生成物 1

HCID 5962624-Chloro-1,5-naphthyridine収率 36%

反応条件

温度
100 °C

実験手順

POCl3 (8.5 ml) was added to [1,5]naphthyridine 1-oxide 483 (0.85 g, 5.81 mmol) at 0° C. and the mixture was heated at 100° C. for 6 h. After cooling, the mixture was concentrated in vacuo, neutralized with NaHCO3 solution and the aqueous phase was extracted with EtOAc (40 ml). The organic phase was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (88:12) as the eluent to give the title compound (0.35 g, 36%).

後処理

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. extractionthe aqueous phase was extracted with EtOAc (40 ml)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with n-hexane/EtOAc (88:12) as the eluent

出典と根拠

ORDレコード
ord-730196c261684ff9ad5320d336ba5b35
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

関連ノート

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