Sodium Hydroxide → HCID 22675488, compound

HRID 1006014Notes

Reaction equation

HRID 1006014 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 (pH1) 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-5f1640390e9a4e20b64909ea4391e562
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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