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

HRID 55354

反応式

HRID 55354 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 97954612-Chloro-3-ethoxycarbonyl-6,7-difluoroquinoline収率 88%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-2971a01b008d4de39939087bd95e35bf
出典データセット
uspto-grants-1997_04
特許番号
US05624933

関連ノート

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