4-Aminopyridine → 4-Pyridylcarbamoyl-beta-alanine ethyl ester

HRID 358555Notes

Reaction equation

HRID 358555 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[N-:8]=[C:9]=[O:10].[CH2:11]([O:13][C:14](=[O:18])[CH2:15][CH2:16]N)[CH3:12]>C(#N)C>[CH2:11]([O:13][C:14](=[O:18])[CH2:15][CH2:16][NH:8][C:9](=[O:10])[NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH3:12]

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 86744639HCID 86744639, compound

Product 1

HCID 200664534-Pyridylcarbamoyl-beta-alanine ethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1 g (10.64 mmol) of 4-aminopyridine and 2.3 g (15.9 mmol) of beta-alanine ethyl ester isocyanate in 30 ml of anhydrous acetonitrile is agitated for 20 hr at room temperature. After concentration to dryness and trituration of the resulting oily residue in ether (4 × 20 ml), 2.5 g (yield 88%) of 4-pyridylcarbamoyl-beta-alanine ethyl ester is obtained in the form of a solid having a melting point of 95° C.

Workup

  1. concentrationAfter concentration to dryness and trituration of the resulting oily residue in ether (4 × 20 ml)

Sources & evidence

ORD record
ord-87a00d5218a444b7b0b074f246b5a9f8
Source dataset
uspto-grants-1991_03
Patent number
US04997667

Reaction notes

Loading…