Benzyloxyamine hydrochloride → 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2105460노트

반응식

HRID 2105460 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][C:13](=O)[CH2:14][CH2:15][CH3:16].Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([O:26][N:27]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]=[C:13]1[CH2:14][CH2:15][CH3:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

4

반응물 2

HCID 102312Benzyloxyamine hydrochlorideHCID 57447109HCID 57447109, 화합물

생성물 1

HCID 675064061-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline수율 29.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of N-(4-chloroquinolin-3-yl)butyramide (3.3 g, 13 mmol, 1.0 eq) and O-benzylhydroxylamine hydrochloride (4.23 g, 26.5 mmol, 2.0 eq) in ethanol (150 mL) was heated at reflux for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane) to provide 1.20 g of 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline.

후처리

  1. temperatureat reflux for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-4764ffd81499413cb32566c89cd248a3
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579359B2

반응 노트

불러오는 중…