Hydrochloric Acid → 5-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

HRID 2397553노트

반응식

HRID 2397553 반응식
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[Cl:13][CH2:14][C:15]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:12])[NH:10]2)=[O:16]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 972508-hydroxyquinolin-2(1H)-oneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

반응 조건

온도
70 °C

실험 절차

27 g of 8-hydroxycarbostyril (VII) and 37 ml of chloroacetyl chloride were dissolved in 250 ml of nitrobenzene, and to the resulting solution was added 85 g of aluminum chloride followed by stirring at 70° C. for 20 hours. 500 ml of 10% aqueous hydrochloric acid was added to the reaction mixture and the nitrobenzene was removed by steam distillation. After cooling the mixture, the precipitated crystals were collected by filtration which were then washed with 300 ml of hot water. Recrystallization from methanol gave 14.0 g of 5-chloroacetyl-8-hydroxycarbostyril (IV) having a melting point of 285°-287° C. (with decomposition) as pale yellow crystals.

후처리

  1. customthe nitrobenzene was removed by steam distillation
  2. temperatureAfter cooling the mixture
  3. filtrationthe precipitated crystals were collected by filtration which
  4. washwere then washed with 300 ml of hot water
  5. customRecrystallization from methanol

출처 및 근거

ORD 기록
ord-06b76146392547ac868d14320262e45e
출처 데이터셋
uspto-grants-1977_05
특허 번호
US04022776

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