3,4-Dinitrophenol → 4-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine

HRID 491650노트

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HRID 491650 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[N+:11]([C:14]1[CH:15]=[C:16]([OH:23])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])([O-:13])=[O:12]>[OH-].[Na+].C(Cl)Cl>[N+:11]([C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[O:23][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12)([O-:13])=[O:12]

참가 물질

5

반응물 2

HCID 113483,4-DinitrophenolHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 177564904-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

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온도
150 °C

실험 절차

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (Step B, 1.0 g, 6.5 mmol) and 3,4-dinitrophenol (1.41 g, 7.6 mmol) was heated at 150° C. for 8 h. The resulting crude solid was dissolved in NaOH (12N) and CH2Cl2. The aqueous layer was extracted several times with CH2Cl2. The insoluble material was solubilized in acetone. The acetone solution was diluted with CH2Cl2 and washed with water. The combined CH2Cl2 layers were dried and concentrated under vacuum. The crude material was purified on silica gel using a CH2Cl2/EtOH gradient (100/0 to 90/10) to give 4-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine.

후처리

  1. extractionThe aqueous layer was extracted several times with CH2Cl2
  2. additionThe acetone solution was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materialThe combined CH2Cl2 layers were dried
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified on silica gel using a CH2Cl2/EtOH gradient (100/0 to 90/10)

출처 및 근거

ORD 기록
ord-533a4370ceca401981bea474b48e0d52
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531553B2

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