Sodium Methoxide → 2-Chloro-N-cyclopropyl-6-methoxyisonicotinamide

HRID 561831Notes

Reaction equation

HRID 561831 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12](Cl)[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:15][O-:16].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:16][CH3:15])[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 215100262,6-Dichloro-N-cyclopropylisonicotinamide

Product 1

HCID 845809352-Chloro-N-cyclopropyl-6-methoxyisonicotinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 2,6-dichloro-N-cyclopropylisonicotinamide from the previous step (1 eq.) in methanol (0.2 M) was added sodium methoxide (6 eq.). The reaction vessel was sealed and the resulting solution was heated in the microwave at 105° C. for 30 min. The volatiles were removed in vacuo and the resulting residue was partitioned between sat. aq. NH4Cl and EtOAc. The organic layer was separated and washed further with brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. customThe reaction vessel was sealed
  2. customThe volatiles were removed in vacuo
  3. customthe resulting residue was partitioned between sat. aq. NH4Cl and EtOAc
  4. customThe organic layer was separated
  5. washwashed further with brine
  6. dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-70df9b98d1eb4805a17df1e360bec669
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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