Water → 2-Methyl-3-nitro-6-[(1-propionylpyrrolidin-3-yl)oxy]pyridine

HRID 390312노트

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HRID 390312 반응식
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[N:3]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH2:25][CH3:26].O>ClCCl>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH:12]2[CH2:16][CH2:15][N:14]([C:24](=[O:27])[CH2:25][CH3:26])[CH2:13]2)[N:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 668835522-Methyl-3-nitro-6-(pyrrolidin-3-yloxy)pyridine

생성물 1

HCID 668832522-Methyl-3-nitro-6-[(1-propionylpyrrolidin-3-yl)oxy]pyridine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

2-Methyl-3-nitro-6-(pyrrolidin-3-yloxy)pyridine (1.3 g) was dissolved in dichloromethane (20 ml) and triethylamine (1.57 ml) was added. The solution was cooled to 0° C. and a solution of propionyl chloride (574 mg) in dichloromethane (5 ml) was added dropwise over 5 min. The reaction mixture was allowed to come to room temperature and was stirred for another 5 min. Water (10 ml) was added. After stirring for 3 min, the phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane/methanol=98/2). Yield: 950 mg (64.9%, pale yellow oil).

후처리

  1. customto come to room temperature
  2. stirringAfter stirring for 3 min
  3. customthe phases were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe combined organic layers were dried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (silica, dichloromethane/methanol=98/2)

출처 및 근거

ORD 기록
ord-7ad4eb3fc29f476aa706b8a2ed8f1dd3
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383641B2

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