Sodium hydride → N-(n-propoxy)-4-methoxy-6-{3-(trifluoromethyl) phenoxy}-2-pyridine carboxamide

HRID 1250505Notes

Reaction equation

HRID 1250505 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:6]=1)=[O:4].[H-].[Na+].[CH2:26](I)[CH2:27][CH3:28]>C1COCC1.C(OCC)(=O)C>[CH2:26]([O:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)[N:6]=1)=[O:4])[CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 18326201N-hydroxy-4-methoxy-6-{3-(trifluoromethyl)phenoxy)-2-pyridine carboxamide

Product 1

HCID 53967309N-(n-propoxy)-4-methoxy-6-{3-(trifluoromethyl) phenoxy}-2-pyridine carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.6 g (0.0018 mol) of N-hydroxy-4-methoxy-6-{3-(trifluoromethyl)phenoxy)-2-pyridine carboxamide was dissolved in THF, and the obtained solution was mixed with 0.08 g (ca. 60% in mineral oil; 0.0018×1.1 mol) of NaH and then with 0.62 g (0.0018×2.0 mol) of n-propyl iodide, followed by treating the solution under reflux for about 2 hours. The reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water and then washed with saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. additionby treating the solution
  2. temperatureunder reflux for about 2 hours
  3. washwashed with saturated brine
  4. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a616b22226ff4b9985ec45dd6cd0fa93
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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