Sodium Azide → 7-(Azidomethyl)-4-chloroquinoline-2-carbonitrile
Reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:15])=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1.[N-:16]=[N+:17]=[N-:18].[Na+]>CCO>[N:16]([CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:15])=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1)=[N+:17]=[N-:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 7-(bromomethyl)-4-chloroquinoline-2-carbonitrile (8.46 g, 30 mmol), sodium azide (2.15 g, 33 mmol) in EtOH (300 mL) was heated under reflux for 1 h. The mixture was then cooled to room temperature and evaporated to dryness. The crude material was purified by flash chromatography (eluting solvent: 100% CH2Cl2 to 5% acetone in CH2Cl2) to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.40 (d, 1H), 8.20 (m, 2H), 7.97 (d, 1H), 4.85 (s, 2H).