Homoallyl bromide → 1,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(3-butenyl)-

A mixture of 1,6-naphthyridine (3.9 g, 0.03 mol) and 4-bromo-1-butene (4.9 g, 0.036 mol) was heated at 70°-80° C. for 5 hours. The reaction mixture was washed with a small quantity of ether, dissolved in methanol (200 ml) and water (60 ml). To the mixture, sodium borohydride (5.7 g, 0.15 mol) was added portionwise over the internal temperature range 0° to 20° C. After stirring overnight at room temperature, the mixture was evaporated in vacuo, water added and extracted with benzene. The benzene layer was dried over anhydrous potassium carbonate and evaporated in vacuo. The resulting residue was purified by alumina column chromatography (eluted successively with petroleum ether, benzene and chloroform) and distilled, bp. 100°-103° C./0.9 mmHg, to afford the Compound No. 14 (1.6 g, 28.4%) as a colorless oil.

1. temperaturewas heated at 70°-80° C. for 5 hours
2. washThe reaction mixture was washed with a small quantity of ether
3. dissolutiondissolved in methanol (200 ml)
4. customrange 0° to 20° C
5. customthe mixture was evaporated in vacuo, water
6. additionadded
7. extractionextracted with benzene
8. dry with materialThe benzene layer was dried over anhydrous potassium carbonate
9. customevaporated in vacuo
10. customThe resulting residue was purified by alumina column chromatography (
11. washeluted successively with petroleum ether, benzene and chloroform) and
12. distillationdistilled
13. custombp. 100°-103° C./0.9 mmHg, to afford the Compound No

ORD record

ord-b916fd3d6df647cea88f3972f3b017f4

Source dataset

uspto-grants-1981_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04308273