Phosphorus oxychloride → 4-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

HRID 422819노트

반응식

HRID 422819 반응식
O[C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 574421684-Hydroxy-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

생성물 1

HCID 666732574-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid수율 60%

반응 조건

온도
85 °C

실험 절차

A mixture of 4-hydroxy-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (876 mg, 4.76 mmol) and POCl3 (4.5 mL) was heated for 24 hours at 85° C. POCl3 was removed under reduced pressure. The crude material was quenched with ice. The reaction mixture was stirred for 1 hour at room temperature. After removing solids by filtration, the aqueous filtrate was extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to give. The recovered material was combined with the solids previously isolated and triturated with ether to afford 577 mg (60%) of the desired product.

후처리

  1. customPOCl3 was removed under reduced pressure
  2. customThe crude material was quenched with ice
  3. customAfter removing solids
  4. filtrationby filtration
  5. extractionthe aqueous filtrate was extracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give
  10. custompreviously isolated
  11. customtriturated with ether

출처 및 근거

ORD 기록
ord-ed0292c6101a4c8797c33ae9fc9c70c4
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101639B2

반응 노트

불러오는 중…