Acetic Anhydride → N-(2,6-dihydroxyphenyl)acetamide

HRID 456403Notes

Reaction equation

HRID 456403 reaction equation
[N+:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11])([O-])=O.[C:12](OC(=O)C)(=[O:14])[CH3:13].[H][H]>[Pd].CO>[OH:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:4]=1[NH:1][C:12](=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 117602-NitroresorcinolHCID 178418361HCID 178418361, compound

Product 1

HCID 22271974N-(2,6-dihydroxyphenyl)acetamideYield 65.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-nitro-1,3-benzenediol (1.55 g 10 mmol), acetic anhydride (1.59 g, 1.47 mL, 15 mmol) and 10% palladium on charcoal (0.3 g) in methanol (100 mL) was stirred in the atmosphere of hydrogen at atmospheric pressure for 2 h. The catalyst was filtered through celite, the solvent evaporated in vacuo. The oily residue was treated with dichloromethane to afford colourless crystals, which were collected by filteration and dried to give the subtitle compound (1.09 g, 65%).

Workup

  1. filtrationThe catalyst was filtered through celite
  2. customthe solvent evaporated in vacuo
  3. additionThe oily residue was treated with dichloromethane
  4. customto afford colourless crystals, which
  5. customwere collected by filteration
  6. customdried

Sources & evidence

ORD record
ord-2a78cc0a20bf41c4904dbc109135be92
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

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