8-Aminoquinoline → 4-Chloroquinolin-8-amine

HRID 1663306ノート

反応式

HRID 1663306 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cl:12]N1C(=O)CCC1=O>CC(O)C>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[Cl:12]

参加物

4

反応物 2

HCID 113598-AminoquinolineHCID 31398Chlorosuccinimide

生成物 1

HCID 126042744-Chloroquinolin-8-amine収率 34%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
25 °C

実験手順

8-amino quinoline (4.5 g, 31.3 mmol), N-chlorosuccinimide (4.80 g, 36 mmol) was taken up in iPrOH (50 mL) at 60° C. The mixture was heated to reflux and stirred for 20 min. The solution was cooled to 25° C. and concentrated to ⅓ original volume. The mixture was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography (5:1 hexanes/EtOAc) to afford 1.90 g (34%) of a 8-amino-4-chloro-quinoline product.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customThe mixture was partitioned between CH2Cl2 and water
  5. extractionThe aqueous layer was extracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (5:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-b7a6a4e82fbe4705bdfc9e68ad8bd688
出典データセット
uspto-grants-2011_10
特許番号
US08034933B2

反応ノート

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