2-Aminopyridine → HCID 14129245, compound

HRID 1762037Notes

Reaction equation

HRID 1762037 reaction equation
[NH2:1][CH:2]([C:8]#[N:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:10]([O-])([O-])OCC.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>C(#N)C>[NH2:9][C:8]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:10]=[N:1][C:2]=1[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 288716Ethyl 2-amino-2-cyanoacetateHCID 53630039Ethylorthoformate

Product 1

HCID 14129245HCID 14129245, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 230 ml of acetonitrile, 8.5 g of ethyl α-aminocyanoacetate, 10.8 g of ethyl orthoformate and 6.2 g of 2-aminopyridine were heated under reflux for 1.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and crystals precipitated were filtered off and washed with benzene to give 11.0 g of the desired compound. m.p.: 129° to 131° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure and crystals
  4. customprecipitated
  5. filtrationwere filtered off
  6. washwashed with benzene

Sources & evidence

ORD record
ord-b4f5b8b8ab13439689182888e5020891
Source dataset
uspto-grants-1989_05
Patent number
US04830660

Reaction notes

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