Water → HCID 23088640, 화합물

HRID 2109069노트

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HRID 2109069 반응식
[Br:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([OH:10])=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:11]([O:10][C:5]1[C:6]([C:8]#[N:9])=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 230887086-Bromo-3-hydroxypyridine-2-carbonitrile

생성물 1

HCID 23088640HCID 23088640, 화합물

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

6-Bromo-3-hydroxypyridine-2-carbonitrile (53.8 g) obtained in Reference Example 72(1) is dissolved in acetone (550 ml), and thereto are added benzyl bromide (35.6 ml) and potassium carbonate (43.1 g). The mixture is then heated under reflux for 4 hours. After allowing to cool, water (600 ml) is added to the reaction solution, and the mixture is extracted with ethyl acetate. The aqueous layer is extracted with ethyl acetate once, and combined with the previous organic layer. The solution is washed with saturated brine and dried over sodium sulfate. The solvent is removed by evaporation under reduced pressure and the residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1, followed by 3/1). The resulting residue is suspended in diethyl ether/n-hexane and the solid is collected by filtration to give the title compound (24.1 g).

후처리

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. extractionthe mixture is extracted with ethyl acetate
  5. extractionThe aqueous layer is extracted with ethyl acetate once
  6. washThe solution is washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is removed by evaporation under reduced pressure
  9. customthe residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1, followed by 3/1)
  10. filtrationthe solid is collected by filtration

출처 및 근거

ORD 기록
ord-a1161280855a4980b9016ccf1e9120cc
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514449B2

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