Benzylamine → N-Benzyl-4-chloropyridine-2-carboxamide

HRID 1252993Notes

Reaction equation

HRID 1252993 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10]C)=O)[CH:3]=1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOCC.CCCCCC>[CH2:12]([NH:19][C:8]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 820890Methyl 4-Chloropicolinate

Product 1

HCID 20137890N-Benzyl-4-chloropyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

A mixture of 5 g of methyl 4-chloropicolinate and 3.44 g of benzylamine is heated at 100° for 16 hours. Cooling and trituration with ether/hexane affords N-benzyl-4-chloro-pyridine-2-carboxamide. This material is heated with 5 g of sodium azide in 50 ml of dimethylformamide at 100° for 10 hours. After dilution with water the product is extracted with ether. Drying and removing the solvent affords 4-azido-N-benzyl-pyridine-2-carboxamide as an oil. This material is stirred under 1 atom of hydrogen in 50 ml of ethanol with 1.0 g of 10% palladium on carbon catalyst for 4 hours. Filtration and removal of solvent affords 4-aminopyridine-2-(N-benzyl)-carboxamide as an oil.

Workup

  1. temperatureis heated at 100° for 16 hours
  2. temperatureCooling

Sources & evidence

ORD record
ord-9f7d60a878574d87a73c7e3b241cb378
Source dataset
uspto-grants-1988_05
Patent number
US04746653

Reaction notes

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