3-Nitrophenol → HCID 20287995, compound

HRID 126782Notes

Reaction equation

HRID 126782 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4].[Cl:13][C:14]1[C:19](Cl)=[N:18][CH:17]=[CH:16][N:15]=1>C(O)C>[Cl:13][C:14]1[C:19]([O:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=2)=[N:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 14798Sodium HydroxideHCID 785752,3-Dichloropyrazine

Product 1

HCID 20287995HCID 20287995, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 250-ml single-necked, round-bottomed flask containing a solution of 3.0 g (75 mmol) of sodium hydroxide in 100 ml of absolute ethanol was added 9.28 g (67 mmol) of 3-nitrophenol at which point the solution turned dark red. To the dark red solution, 10.0 g (66 mmol) of 2,3-dichloropyrazine was added and the resulting solution refluxed for 162 hours. The reaction mixture was cooled and concentrated. Upon pouring the concentrate into approximately 300 ml of water, an off-white solid precipitated which was collected by filtration. Recrystallization from absolute ethanol gave the product, 2-chloro-3-(3-nitrophenoxy)pyrazine, (46% yield) as white needles, mp 119°-121° C.

Workup

  1. temperaturethe resulting solution refluxed for 162 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. additionUpon pouring the
  5. concentrationconcentrate into approximately 300 ml of water
  6. customan off-white solid precipitated which
  7. filtrationwas collected by filtration
  8. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-d0be66b2fc944091853bf40e48a5cbc6
Source dataset
uspto-grants-1981_03
Patent number
US04254125

Reaction notes

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