Sodium Azide → HCID 118366172, compound

HRID 59899Notes

Reaction equation

HRID 59899 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CO.O>[N:13]([CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]=1)=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 29921712Methyl 4-(bromomethyl)pyridine-2-carboxylate

Product 1

HCID 118366172HCID 118366172, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To solution of methyl 4-(bromomethyl)picolinate (350 mg, 1.52 mmol) in methanol (5 mL) was added a solution of sodium azide (198 mg, 3.04 mmol) in water (0.5 mL). The mixture was heated to reflux for 2 hours, then was concentrated. The resulting residue was dissolved in EtOAc (10 mL) and water (10 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give methyl 4-(azidomethyl)picolinate (280 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationwas concentrated
  4. dissolutionThe resulting residue was dissolved in EtOAc (10 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b8891fee1ec443cc8d2976d6f0e7124f
Source dataset
uspto-grants-2016_09
Patent number
US09440949B2

Reaction notes

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