2-Aminophenol → HCID 57548517, compound

HRID 333021Notes

Reaction equation

HRID 333021 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([O-])(=O)C.[Na+].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:18]=1Cl)([O-:16])=[O:15]>C(O)C>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:18]=1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 118141-Chloro-2,6-dinitrobenzeneHCID 517045Sodium Acetate

Product 1

HCID 57548517HCID 57548517, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17.30 g (157 mmol) of 99% strength 2-aminophenol and 17.15 g (209 mmol) of anhydrous sodium acetate are added to a solution of 25.0 g (121 mmol) of 98% strength 2,6-dinitrochlorobenzene in 185 ml of anhydrous ethanol under nitrogen while stirring. The reaction solution is refluxed for 2 hours and subsequently cooled to room temperature. The red-violet crystalline needles are separated off on a “black band” filter, washed with water until the washings are colorless and dried at 50° C. under reduced pressure. This gives 27.90 g (84% of theory) of shiny black needles which melt at 189-192° C. (lit.: 191° C.).

Workup

  1. temperatureThe reaction solution is refluxed for 2 hours
  2. customThe red-violet crystalline needles are separated off on a “black band”
  3. filtrationfilter
  4. washwashed with water until the washings
  5. customdried at 50° C. under reduced pressure
  6. custommelt at 189-192° C.
  7. custom(lit.: 191° C.)

Sources & evidence

ORD record
ord-a632b9b5b0e845a59c358f82262ab750
Source dataset
uspto-grants-2014_11
Patent number
US08877937B2

Reaction notes

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