Sodium Hydroxide → 2-Chloro-6-fluoroquinoline

HRID 860023ノート

反応式

HRID 860023 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 150594332-Chloro-6-fluoroquinoline

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-db4f91d21adc4a57b597d344b7604f66
出典データセット
uspto-grants-2006_12
特許番号
US07153849B2

反応ノート

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