O-ethylhydroxylamine hydrochloride → 1-ethoxy-1H-imidazo[4,5-c]quinoline

HRID 2105480노트

반응식

HRID 2105480 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][CH:13]=O.Cl.[CH2:16]([O:18][NH2:19])[CH3:17]>C(O)(C)C>[CH2:16]([O:18][N:19]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[CH:13]1)[CH3:17]

참가 물질

4

반응물 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 86227468N-(4-chloroquinolin-3-yl)formamide

생성물 1

HCID 675069551-ethoxy-1H-imidazo[4,5-c]quinoline수율 47.9%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of 4-chloroquinolin-3-ylformamide (5.0 g, 24 mmol), O-ethylhydroxylamine hydrochloride (2.95 g, 30.2 mmol), and isopropanol (75 mL) was heated at reflux overnight, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was stirred with dichloromethane (150 mL) and saturated aqueous sodium carbonate (50 mL) for 15 minutes. The organic layer was separated and dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent) to provide 2.45 g of 1-ethoxy-1H-imidazo[4,5-c]quinoline.

후처리

  1. temperatureat reflux overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe organic layer was separated
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent)

출처 및 근거

ORD 기록
ord-a91af1a69f174bea8db4f7f02889b41c
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579359B2

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