3,4-Dinitrophenol → 4-(3,4-Dinitrophenoxy)-pyridine

HRID 491579Notes

Reaction equation

HRID 491579 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[CH:12]=[C:13]([OH:20])[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])([O-:10])=[O:9].Cl.O1CCOCC1.[OH-].[Na+]>CCOC(C)=O.Cl.O>[N+:8]([C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[O:20][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 113483,4-DinitrophenolHCID 122884-ChloropyridineHCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 177560774-(3,4-Dinitrophenoxy)-pyridine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21885828Hydrate;hydrochlorideSolvent

Conditions

Temperature
145 °C

Procedure

4-Chloropyridine (3.20 g, 28.2 mmol) and 3,4-dinitrophenol (5.96 g, 32.4 mmol) were combined in an open round-bottom flask fitted with running water condenser. The reaction flask was heated to 145° C. After 45 min, 4N HCl/dioxane (2.1 mL) was added. The reaction was heated for an additional 25 min then cooled to RT. The mix was dissolved in EtOAc and 0.5 N HCl/water. The aqueous layer was basified with 6 N NaOH. A beige solid was isolated and identified as title compound.

Workup

  1. customfitted with running water condenser
  2. temperatureThe reaction was heated for an additional 25 min
  3. temperaturethen cooled to RT
  4. customA beige solid was isolated

Sources & evidence

ORD record
ord-3d9ce4d4a5ba4a3f8afc630eaf4acf43
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

Loading…