8-Aminoquinoline → 4-Chloroquinolin-8-amine

HRID 2117286노트

반응식

HRID 2117286 반응식
[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]

참가 물질

4

반응물 2

HCID 113598-AminoquinolineHCID 31398Chlorosuccinimide

생성물 1

HCID 126042744-Chloroquinolin-8-amine수율 34%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
25 °C

실험 절차

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-chloroquinoline product.

후처리

  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)

출처 및 근거

ORD 기록
ord-266e9d664e2440f59b300a3b71348da4
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442703B2

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