Ethyl Acetate → Methyl 6-(azidomethyl)nicotinate

HRID 347629Notes

Reaction equation

HRID 347629 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+].CCOC(C)=O>CN(C=O)C>[N:13]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 127522376-Bromomethyl-nicotinic acid methyl ester

Product 1

HCID 22565575Methyl 6-(azidomethyl)nicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 6-(bromomethyl)nicotinate from Example G1 (2.0 g, 8.60 mmol) in DMF (15 ml) was added sodium azide (0.84 g, 12.9 mmol). The mixture was stirred at room temperature for 18 h. EtOAc (100 ml) was added and the mixture was washed with water (3 times), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet ether 20:80) to give a yellow gum; yield 1.55 g (93%).

Workup

  1. washthe mixture was washed with water (3 times)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica (eluant EtOAc:pet ether 20:80)
  5. customto give a yellow gum

Sources & evidence

ORD record
ord-77910342e3c14ec883483cc46137b415
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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