Sodium Azide → HCID 470749, compound

Participants

Reaction Conditions

Reaction Steps

8-[2-(3-Aminophenyl)ethyl]-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.22 g, 0.54 mmol) was dissolved in 0.55 mL of concentrated hydrochloric acid. Water (2.8 mL) was added and the solution was cooled to 0° C. producing a precipitate. A solution of sodium nitrite (0.19 g, 2.75 mmol) in 8 mL of water was added dropwise. After 20 min, a solution of sodium azide (0.27 g, 4.15 mmol) in 3 mL of water was added in the dark. After 15 min, the product was extracted with ethyl acetate. Purification by flash chromatography, eluting with ethyl acetate/hexanes, and recrystallization (ether/petroleum ether) afforded 0.17 g of the title compound, m.p. 104°-105° C.

Provenance & Evidence