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

HRID 513749노트

반응식

HRID 513749 반응식
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

참가 물질

3

반응물 2

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

생성물 1

HCID 5962624-Chloro-1,5-naphthyridine수율 36%

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-730196c261684ff9ad5320d336ba5b35
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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