Ammonium formate → 4-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide

HRID 1921811Notes

Reaction equation

HRID 1921811 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:4]=1[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:6].C([O-])=O.[NH4+]>CCO.CCOC(C)=O.[Pd]>[NH2:20][C:18]1[CH:17]=[CH:16][C:4]([C:5]([NH:7][CH2:8][C:9]2[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[O:6])=[C:3]([O:2][CH3:1])[CH:19]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 575899912-Methoxy-N-(6-methylpyridin-3-yl)methyl-4-nitrobenzamide

Product 1

HCID 575900544-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methoxy-N-(6-methylpyridin-3-yl)methyl-4-nitrobenzamide (448 mg, 1.49 mmol) in EtOH and EtOAc (8 mL each) is stirred and ammonium formate (375 mg, 6 mmol) and 10% Pd/C (100 mg) are added. The mixture is heated at reflux for 20 min, cooled, filtered through celite, the solid is washed with EtOH and the combined solvents are evaporated to afford the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 20 min
  3. temperaturecooled
  4. filtrationfiltered through celite
  5. washthe solid is washed with EtOH
  6. customthe combined solvents are evaporated

Sources & evidence

ORD record
ord-76722e8d2b004ce3a5179e597379bc7a
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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