Acetic Acid → HCID 3771453, compound

HRID 366435Notes

Reaction equation

HRID 366435 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][C:4]=1[OH:12].[CH3:13]C(O)=O>CO.[Pd]>[CH3:1][N:2]1[C:3]2[C:4]([OH:12])=[CH:5][CH:6]=[CH:7][C:8]=2[N:9]=[CH:13]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 36007202-(methylamino)-3-nitrophenol

Product 1

HCID 3771453HCID 3771453, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methylamino-3-nitrophenol (1.00 g, 5.98 mmol) in MeOH (100 mL) with HOAc (0.22 mL) was hydrogenated (50 psi) for 2 hours over 10% Pd on carbon (186 mg). The catalyst was removed by filtration and the filtrate concentrated in vacuo. The residue was dissolved in formic acid and refluxed for 17 hours under N2 (g). Excess acid was removed in vacuo, and the residue was taken up in 5% MeOH in EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was taken up in 5% MeOH in EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated in vacuo to yield a red-brown solid which was chromatographed on silica (50-100% EtOAc/hexanes). The desired product (GC/MS m/z 148) was obtained as a yellow solid, 0.748 g; 84%.

Workup

  1. customfor 2 hours
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. dissolutionThe residue was dissolved in formic acid
  5. temperaturerefluxed for 17 hours under N2 (g)
  6. customExcess acid was removed in vacuo
  7. washwashed with saturated aqueous NaHCO3 and brine
  8. dry with materialThe organic phase was dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. washwashed with saturated aqueous NaHCO3 and brine
  11. dry with materialThe organic phase was dried over Na2SO4
  12. concentrationconcentrated in vacuo
  13. customto yield a red-brown solid which
  14. customwas chromatographed on silica (50-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a85685c19444452881200129dcac09c1
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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