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

HRID 922767Notes

Reaction equation

HRID 922767 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

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 667895247-(Bromomethyl)-4-chloroquinoline-2-carbonitrile

Product 1

HCID 597748847-(Azidomethyl)-4-chloroquinoline-2-carbonitrileYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperaturethe resulting slurry mixture was refluxed for 1 h
  2. filtrationThe resulting solid was collected by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-37d4dfab9c8e4c86912efb217b5dcfcc
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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