Phosphorus trichloride → 2-Chloro-3-ethoxycarbonyl-6,7-difluoroquinoline

HRID 55354

반응식

HRID 55354 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[N:8](O)[C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([F:16])=[C:11]([F:17])[CH:10]=2)=[O:5])[CH3:2].C(OC(C1C(=O)NC2C(C=1)=CC(F)=C(F)C=2)=O)C.P(Cl)(Cl)[Cl:39].P(Cl)(Cl)(Cl)=O>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:39])=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([F:16])=[C:11]([F:17])[CH:10]=2)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 24387Phosphorus trichlorideHCID 24813Phosphorus oxychlorideHCID 152943803-Ethoxycarbonyl-6,7-difluoro-1-hydroxy-2-oxoquinolineHCID 199573073-Ethoxycarbonyl-6,7-difluorocarbostyril

생성물 1

HCID 97954612-Chloro-3-ethoxycarbonyl-6,7-difluoroquinoline수율 88%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
0 °C

실험 절차

A mixture of 3-ethoxycarbonyl-6,7-difluoro-1-hydroxy-2-oxoquinoline (25 g at a concentration of 75 mol %, equivalent to 69.65 mmol), 3-ethoxycarbonyl6,7-difluoro-2-oxoquinoline (25 g at a concentration of 5 mol %, equivalent to 4.9 mmol), phosphorus trichloride (59.6 g, equivalent to 433.5 mmol) and phosphoryl chloride (15.05 g, equivalent to 98.05 mmol) in 1,2-dichloroethane (170 cm3) is heated at reflux for 3 hours. After cooling to 0° C., the reaction mixture is poured onto slushed ice (250 g of ice +250 g of water at 0° C.) and left to separate overnight. The organic phase is washed with saturated NaHCO3 solution (100 cm3), followed by water (100 cm3), and then concentrated to dryness in order to obtain 19.8 g of 3-ethoxycarbonyl-6,7-difluoro-2-chloroquinoline of 90% assay (HPLC), equivalent to a yield of 88%.

후처리

  1. temperatureat reflux for 3 hours
  2. waitleft
  3. customto separate overnight
  4. washThe organic phase is washed with saturated NaHCO3 solution (100 cm3)
  5. concentrationconcentrated to dryness in order

출처 및 근거

ORD 기록
ord-2971a01b008d4de39939087bd95e35bf
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624933

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