Acetic Anhydride → HCID 66628388, compound

HRID 132593Notes

Reaction equation

HRID 132593 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([OH:10])[C:3]=1[N+:11]([O-])=O.[C:14](OC(=O)C)(=[O:16])[CH3:15]>CO.[Pd]>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([OH:10])[C:3]=1[NH:11][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 12190870HCID 12190870, compound

Product 1

HCID 66628388HCID 66628388, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,6-Dihydroxy-4-methoxynitrobenzene (0.60 g, 3.24 mmol) was hydrogenated in the presence of acetic anhydride (0.29 g, 4.86 mmol) and 10% Pd/C (0.2 g) in methanol (30 mL) under atmospheric pressure and room temperature. The catalyst was removed by filtration through a pad of celite and the the crude product was purified by flash chromatography (SiO2, Toluene-ethyl acetate, 3:3 then 1:2) to afford the subtitle compound (0.43 g, 67.9%).

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. customthe the crude product was purified by flash chromatography (SiO2, Toluene-ethyl acetate, 3:3

Sources & evidence

ORD record
ord-8b0ecb4e2de249cfb1d5c314cceaf5a1
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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