Sodium Azide → HCID 57707899, compound

HRID 216863Notes

Reaction equation

HRID 216863 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[C:8]([CH2:19]Cl)=[CH:7]2.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH2:19][C:8]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[Cl:1])=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57707798HCID 57707798, compound

Product 1

HCID 57707899HCID 57707899, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To stirring solution of 8-chloro-3-(chloromethyl)-2-(2-fluorophenyl)quinoline (0.330 g, 1.08 mmol) in DMF was added sodium azide (0.561 g, 8.62 mmol), and the mixture stirred at room temperature. After 3 hours, the mixture was partitioned between CH2Cl2 and H2O. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure: LC-MS (ESI) m/z 313.0 [M+H]+. The crude product was carried on crude without purification for the next step.

Workup

  1. customthe mixture was partitioned between CH2Cl2 and H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was carried on crude without purification for the next step

Sources & evidence

ORD record
ord-96fbf0b902264d98af642abe5467698c
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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