2-Aminopyridine → HCID 178515422, compound

HRID 1112522Notes

Reaction equation

HRID 1112522 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C([O:18][CH:19]=[C:20]([C:26]#[N:27])[C:21](OCC)=O)C>O1CCCC1>[NH:5]1[C:26]([C:20]2[C:19](=[O:18])[N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]3=[N:9][CH:21]=2)=[N:27][N:7]=[N:6]1

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 33557Sodium AzideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178515422HCID 178515422, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (1.73 g., 12.96 mmoles) was added to tetrahydrofuran (45 ml.) at -20°. Sodium azide (2.52 g., 38.71 mmoles) was then added and the mixture heated under reflux for 40 minutes. To this mixture was added 2-aminopyridine (1.0 g., 10.62 mmoles) and ethyl ethoxymethylenecyanoacetate (1.8 g., 10.62 mmoles). The mixture was heated under reflux for 18 hours. The mixture was concentrated and the residue treated with water (50 ml.). The mixture was acidified to pH 3 with 6N hydrochloric acid. The solid material was collected and suspended in 3% aqueous sodium bicarbonate. The mixture was heated under reflux for 5 minutes, filtered, and the filtrate acidified to pH 4 with 6N hydrochloric acid. The precipitate was recrystallized from N,N-dimethylformamide to give the title compound (0.35 g., 15.4%), m.p. 312°-313° (decomp).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 40 minutes
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 18 hours
  5. concentrationThe mixture was concentrated
  6. additionthe residue treated with water (50 ml.)
  7. customThe solid material was collected
  8. temperatureThe mixture was heated
  9. temperatureunder reflux for 5 minutes
  10. filtrationfiltered
  11. customThe precipitate was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-6cfd725b15ab41829db020e49e195d80
Source dataset
uspto-grants-1978_10
Patent number
US04122274

Reaction notes

Loading…