5-tert-Butyl-3-nitropyridin-2(1H)-one → HCID 58980663, compound

HRID 735793Notes

Reaction equation

HRID 735793 reaction equation
[N+:1]([C:4]1[C:5](=[O:14])[NH:6][CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1)([O-])=O>CO.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[C:5](=[O:14])[NH:6][CH:7]=[C:8]([C:10]([CH3:12])([CH3:11])[CH3:13])[CH:9]=1

Participants

4

Reactant 1

HCID 206071765-tert-Butyl-3-nitropyridin-2(1H)-one

Product 1

HCID 58980663HCID 58980663, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

3-Nitro-5-tert-butyl-1H-pyridin-2-one (360 mg, 1.83 mmol) was dissolved in methanol/ethyl acetate (2:1, 3 mL) and placed in a Parr hydrogenation vessel. Pd (10% on carbon, 36 mg) was added and the reaction was placed under a hydrogen atmosphere (50 psi) and shaken at room temperature for 2 h. The solution was then filtered through diatomaceous earth and concentrated in vacuo. The residue was redissolved in diethyl ether and extracted (3×) with 1.0 M HCl. The pH of the combined aqueous layers was adjusted to 10 with NaHCO3 and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide 3-amino-5-tert-butyl-1H-pyridin-2-one (195 mg, 64%) as a pale green solid: ESI MS m/z 166 [C9H14N2O+H]+.

Workup

  1. filtrationThe solution was then filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was redissolved in diethyl ether
  4. extractionextracted (3×) with 1.0 M HCl
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f79751f9b859495eb85e7b90e5693056
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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