2,6-Dinitrophenol → 2-Amino-6-nitrophenol

HRID 1528187Notes

Reaction equation

HRID 1528187 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[OH:13])([O-:3])=[O:2]>C(OCC)(=O)C>[NH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[OH:13]

Participants

3

Reactant 1

HCID 113122,6-Dinitrophenol

Product 1

HCID 51272912-Amino-6-nitrophenolYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8.6 g of 2,6-dinitrophenol (46.71 mmol) were dissolved in 95 ml of ethyl acetate. The solution was degassed and then 0.86 g (10% by weight) of palladium on carbon at 10% was added. The reaction medium was stirred under a hydrogen atmosphere for 6 days at ambient temperature. The reaction medium was filtered through celite and concentrated to dryness. The residue obtained was chromatographed on a cartridge of silica gel eluted with 100% dichloromethane to 80/20 dichloromethane/ethyl acetate. 3.43 g of product were obtained in the form of a dark copper solid. Yield=48%.

Workup

  1. customThe solution was degassed
  2. addition0.86 g (10% by weight) of palladium on carbon at 10% was added
  3. filtrationThe reaction medium was filtered through celite and
  4. concentrationconcentrated to dryness
  5. customThe residue obtained
  6. customwas chromatographed on a cartridge of silica gel
  7. washeluted with 100% dichloromethane to 80/20 dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-d6b9bdcbe1d94226ac25a5d8bcb8bece
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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