Triethylamine → 2-Amino-N-[(4-methoxyphenyl)methyl]-3-pyridinecarboxamide

HRID 2187053Notes

Reaction equation

HRID 2187053 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>CN(C)C=O>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:35][CH2:34][C:33]1[CH:36]=[CH:37][C:30]([O:29][CH3:28])=[CH:31][CH:32]=1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 729302-Aminonicotinic acidHCID 754524-MethoxybenzylamineHCID 76257Diethyl cyanophosphonate

Product 1

HCID 224497462-Amino-N-[(4-methoxyphenyl)methyl]-3-pyridinecarboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Aminonicotinic acid (7.15 g) was suspended in N,N-dimethylformamide (100 ml) and 4-methoxybenzylamine (8.12 ml), diethyl cyanophosphonate (9.92 ml) and triethylamine (8.66 ml) were added sequentially with stirring and cooling on ice. The reaction mixture was stirred at room temperature for 15.5 hours, concentrated under reduced pressure, and extracted with ethyl acetate. The extract was washed with water, dried (Na2SO4) and then the solvent was distilled off under reduced pressure to give the title compound (15.9 g, about 100%). Recrystallization from ethyl acetate-ethyl ether yielded a colorless crystal, melting point 165 to 166° C.

Workup

  1. temperaturecooling on ice
  2. stirringThe reaction mixture was stirred at room temperature for 15.5 hours
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried (Na2SO4)
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b29022018ffe4c4e863ca82c73e47cff
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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