6-chloro-N-(4-propan-2-ylphenyl)pyridine-3-carboxamide → N-(4-isopropylphenyl)-6-methoxypyridine-3-carboxamide

HRID 218545Notes

Reaction equation

HRID 218545 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:20][O-:21].[Na+]>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[N:15][C:16]([O:21][CH3:20])=[CH:17][CH:18]=2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24739216-chloro-N-(4-propan-2-ylphenyl)pyridine-3-carboxamideHCID 10942334Sodium Methoxide

Product 1

HCID 17854296N-(4-isopropylphenyl)-6-methoxypyridine-3-carboxamideYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

N-(4-Isopropylphenyl)-6-chloropyridine-3-carboxamide (1.00 g) was dissolved in THF (10 mL) and sodium methoxide (0.21 g) was added. The mixture was stirred at 50° C. for one day. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give N-(4-isopropylphenyl)-6-methoxypyridine-3-carboxamide (0.76 g).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e8e89d325034c3d935b819f9729bf65
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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