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

HRID 491650ノート

反応式

HRID 491650 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-533a4370ceca401981bea474b48e0d52
出典データセット
uspto-grants-2009_05
特許番号
US07531553B2

反応ノート

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