Ammonium formate → N-(5-aminopyridin-2-yl)-2-phenylacetamide

HRID 1366196Notes

Reaction equation

HRID 1366196 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>CCO.CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:19])[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:8][CH:9]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 4350143N-(5-nitropyridin-2-yl)-2-phenylacetamide

Product 1

HCID 43144587N-(5-aminopyridin-2-yl)-2-phenylacetamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(5-nitropyridin-2-yl)-2-phenylacetamide (4.35 g, 16.9 mmol) in EtOH (75 mL) and EtOAc (75 mL) is stirred at rt and ammonium formate (4.27 g) and 10% Pd/C (500 mg) are added. The mixture is heated at reflux for 30 min, cooled, filtered through celite and evaporated to afford the title compound as an off-white solid which was used without further purification.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 30 min
  3. temperaturecooled
  4. filtrationfiltered through celite
  5. customevaporated

Sources & evidence

ORD record
ord-196008d43ba04aa4a74677cbf4558bf4
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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