1,4-Dioxane → Methyl 6-chloronicotinimidate

HRID 1020958Notes

Reaction equation

HRID 1020958 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][N:6]=1.[O:13]1CCOC[CH2:14]1>CO.CCOC(C)=O.O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[NH:12])[O:13][CH3:14])=[CH:7][N:6]=1

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 86762380Methyl 6-chloronicotinimidate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium methoxide (725 mg, 13.42 mmol) was added to a solution of 2-Chloro pyridine-5-carbonitrile (1.8 g, 13.04 mmol) in MeOH:dioxane (40 ml, 1:1) at 0° C., then stirred for 30 minutes at 0° C., and 1 hour at room temperature. The reaction was diluted with EtOAc (200 ml) and H2O (100 ml), organic layer separated, dried over Na2SO4, filtered and solvent evaporated to yield title compound 1BX as a white solid (2.6 g, 100%) MS (MH 171)

Workup

  1. custom1 hour
  2. customat room temperature
  3. customseparated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customsolvent evaporated

Sources & evidence

ORD record
ord-3615d29780be4a3081082198416b1932
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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