Sodium Azide → 7-(Azidomethyl)-4-chloroquinoline-2-carbonitrile

HRID 2422537Notes

Reaction equation

HRID 2422537 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

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

Product 1

HCID 597748847-(Azidomethyl)-4-chloroquinoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. customevaporated to dryness
  4. customThe crude material was purified by flash chromatography (eluting solvent: 100% CH2Cl2 to 5% acetone in CH2Cl2)

Sources & evidence

ORD record
ord-bd7ed27b5e89498fb1109e9c6fe19952
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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