2-Bromoethanol → 7-Chloro-6-fluoro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, ethyl ester

HRID 1578278ノート

反応式

HRID 1578278 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][NH:9]2)=[CH:4][C:3]=1[F:18].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][OH:28]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][N:9]2[CH2:26][CH2:27][OH:28])=[CH:4][C:3]=1[F:18]

参加物

5

反応物 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 3018009Ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

生成物 1

HCID 6178607-Chloro-6-fluoro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, ethyl ester収率 67%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A solution of 8.1 g of 7-chloro-3-ethoxycarbonyl-6-fluoro-4-oxo-1,4-dihydro-quinoline and 8.2 g of potassium carbonate in 70 cm3 of DMF was agitated and heated at 110° C. for 1 hour. After cooling to 60° C., 15 of 2-bromo-ethanol were added to the reaction mixture and it was agitated and heated at 110° C. for 4 hours. After evaporation of the solvent under reduced pressure, 100 cm3 of water were added to the residue and the aqueous mixture was extracted with chloroform (4×100 cm3). The combined organic extracts were washed with water (2×100 cm3), dried over Na2SO4, filtered and then evaporated to dryness. The residue was recrystallised from ethanol (150 cm3). 6.75 g of 7-chloro-6-fluoro-3-ethoxycarbonyl-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline, m.p. 202° C., were obtained; yield 67%.

後処理

  1. temperatureAfter cooling to 60° C.
  2. temperatureheated at 110° C. for 4 hours
  3. customAfter evaporation of the solvent under reduced pressure, 100 cm3 of water
  4. additionwere added to the residue
  5. extractionthe aqueous mixture was extracted with chloroform (4×100 cm3)
  6. washThe combined organic extracts were washed with water (2×100 cm3)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was recrystallised from ethanol (150 cm3)

出典と根拠

ORDレコード
ord-abeac1a068eb430faa54fd320b1d5d82
出典データセット
uspto-grants-1981_09
特許番号
US04292317

反応ノート

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