Sodium Azide → HCID 58081357, compound

HRID 928440Notes

Reaction equation

HRID 928440 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[N:4]=1.[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[N:14]([CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[N:4]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 102441602-(Bromomethyl)-7-chloroquinoline

Product 1

HCID 58081357HCID 58081357, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(bromomethyl)-7-chloroquinoline (50 mg, 0.195 mmol) in DMF (0.5 ml) was added sodium azide (19.01 mg, 0.292 mmol). Reaction mixture was stirred for 2 h at 90° C. Reaction mixture was diluted with ethyl acetate/water. Layers were separated and organic layer was washed twice with water and with brine, dried over sodium sulfate, filtered and evaporated to afford the title compound. HPLC (Method G) Rt=1.990 min, MS (Method V) [M+H]+=219.1.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. customLayers were separated
  4. washorganic layer was washed twice with water and with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f9ef84d99399461db2b2c7be6951fbd7
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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