Sodium Hydroxide → HCID 22254517, 화합물

HRID 434005

반응식

HRID 434005 반응식
[N:1]1([CH:14]([CH2:17][CH3:18])[CH2:15][OH:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.Br[C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:21]=1[CH3:28].[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[N:1]1([CH:14]([CH2:17][CH3:18])[CH2:15][O:16][CH2:28][C:21]2[CH:20]=[CH:25][C:24]([C:26]#[N:27])=[CH:23][CH:22]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 140048403-Bromo-4-methylbenzonitrileHCID 218980232-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol

생성물 1

HCID 22254517HCID 22254517, 화합물수율 60.2%

시약·촉매·용매 3

HCID 5963Benzyltrimethylammonium chloride촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

2-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol (3.0 g, 12.4 mmol) was added to a stirring mixture of cc-bromo-p-tolunitrile (3.0 g, 15.3 mmol), sodium hydroxide (40 ml, 50%), dichloromethane (40 ml), and benzyltrimethylammonium chloride (0.02 g, 0.11 mmol). The reaction was maintained for 72 hours and then diluted with dichloromethane (100 ml) and water (100 ml). The phases were separated and the aqueous phase was extracted with additional dichloromethane (100 ml). The organic fractions were combined, washed with water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol, Rf0.48) to provide 2.66 g of 4-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)butoxy]methyl}benzonitrile.

후처리

  1. temperatureThe reaction was maintained for 72 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with additional dichloromethane (100 ml)
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol, Rf0.48)

출처 및 근거

ORD 기록
ord-e012e80795af4fd1b38d7c43054bad18
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670372B2

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