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

HRID 491650Notes

Reaction equation

HRID 491650 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-533a4370ceca401981bea474b48e0d52
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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