Sodium Azide → 7-(Azidomethyl)-2-chloro-4-(4-fluorophenyl)quinoline

HRID 2422551Notes

Reaction equation

HRID 2422551 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:8][C:9]([Cl:13])=[N:10]2)=[CH:5][CH:4]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>C(O)C>[N:21]([CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:8][C:9]([Cl:13])=[N:10]2)=[CH:5][CH:4]=1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866219797-(Bromomethyl)-2-chloro-4-(4-fluorophenyl)quinoline

Product 1

HCID 866219807-(Azidomethyl)-2-chloro-4-(4-fluorophenyl)quinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-(bromomethyl)-2-chloro-4-(4-fluorophenyl)quinoline (1.0 g, 2.9 mmol) and sodium azide (204 mg, 3.1 mmol) in ethanol (40 mL) was refluxed for 16 h. The solution was concentrated and dichloromethane was added. The mixture was filtered, and concentrated to give the title compound. MS (+ESI): 313 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. additiondichloromethane was added
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-98ebb13334d54635b425cccd7baa1047
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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