Sodium Hydroxide → 2-Chloro-6-fluoroquinoline

HRID 860023노트

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HRID 860023 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH:6]=[CH:5]2.P(Cl)(Cl)([Cl:15])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 98340436-Fluoro-1,2-dihydroquinolin-2-one

생성물 1

HCID 150594332-Chloro-6-fluoroquinoline

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
95 °C

실험 절차

A mixture of 6-fluoroquinolin-2(1H)-one from Step C, (0.971 g, 6 mmol), phosphorous oxychloride (2.83 mL, 30 mmol), and toluene (20 mL) is heated at 95° C. for 2 hours. The reaction is cooled in an ice bath and basified with 50% aqueous sodium hydroxide. The mixture is extracted with ethyl acetate and the extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated to an orange solid (1.01 g). The residue is flash chromatographed on silica gel Merck-60 with 5% ethyl acetate in hexane to provide the title compound as a light pink solid, m.p. 99–101° C.

후처리

  1. temperatureThe reaction is cooled in an ice bath
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe extracts are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an orange solid (1.01 g)
  6. customchromatographed on silica gel Merck-60 with 5% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-db4f91d21adc4a57b597d344b7604f66
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153849B2

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