Sodium Hydroxide → HCID 22675488, compound

HRID 1106807Notes

Reaction equation

HRID 1106807 reaction equation
[CH2:1]([N:3]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[CH:20][N:19]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([N:3]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][N:19]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22675520HCID 22675520, compound

Product 1

HCID 22675488HCID 22675488, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(N-ethyl-N-(2-phenoxybenzyl)amino)pyridine-5-carboxylate (0.65 g, 1.74 mmol) in THF (3 ml) and methanol (3 ml) was treated with aqueous sodium hydroxide (1N, 4 ml). The reaction mixture was heated at reflux for 3 hours cooled to ambient and allowed to stand for 60 hours, then heated at reflux for 3 hours. The organic solvent was evaporated, the residue diluted with water and acidified (pHi) with HCl (conc.). The aqueous suspension was extracted with ethyl acetate, the organic phase was dried (MgSO4) and evaporated and the solid was recrystallized from ethyl acetate/water and dried under reduced pressure to give the title product.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. temperatureheated
  5. temperatureat reflux for 3 hours
  6. customThe organic solvent was evaporated
  7. additionthe residue diluted with water
  8. extractionThe aqueous suspension was extracted with ethyl acetate
  9. dry with materialthe organic phase was dried (MgSO4)
  10. customevaporated
  11. customthe solid was recrystallized from ethyl acetate/water
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-eb68fa3df1ec4dcdaf660283455459b8
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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