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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).

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