Water → 7-(Azidomethyl)-4-chloroquinoline-2-carbonitrile

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([Cl:19])=[CH:12][C:13]([C:17]#[N:18])=[N:14]2)=[CH:9][CH:8]=1.O>CCO>[N:1]([CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([Cl:19])=[CH:12][C:13]([C:17]#[N:18])=[N:14]2)=[CH:9][CH:8]=1)=[N+:2]=[N-:3]

Participants

Procedure

Sodium azide (1.690 g, 26.0 mmol, 1.3 equiv.) was added to a stirred solution of 7-(bromomethyl)-4-chloroquinoline-2-carbonitrile (2-4, 5.63 g, 20.00 mmol) in 100 ml of EtOH, and the resulting slurry mixture was refluxed for 1 h. The mixture was cooled to rt, water (100 ml) was added, and the slurry was stirred at rt for 30 min. The resulting solid was collected by filtration and air dried to afford 7-(azidomethyl)-4-chloroquinoline-2-carbonitrile (3-12, 4.75 g, 97%) as a white solid. LRMS m/z (M+H)+ 244.1 found, 244.65 required.