Sodium Hydroxide → HCID 68633995, compound

HRID 2196434Notes

Reaction equation

HRID 2196434 reaction equation
[OH-].[Na+].[C:3]([O:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([NH:21]C(=O)C)=[N:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4]>C(O)C.O>[C:3]([O:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68631622HCID 68631622, compound

Product 1

HCID 68633995HCID 68633995, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

559 mg of sodium hydroxide in 2 ml of ethanol and 2 ml of water are placed in a round-bottomed flask containing 695 mg of N-[5-(3-tert-butoxymethylphenyl)pyridin-2-yl]acetamide. 1 ml of water and 1 ml of ethanol are added thereto and the mixture is heated at the reflux of the solvent for 1 hour. After cooling, the reaction mixture is concentrated under reduced pressure. The residue is taken up between dichloromethane and water and the organic phase is then separated, dried over magnesium sulphate and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 487 mg of compound are obtained.

Workup

  1. temperaturethe mixture is heated at the
  2. temperaturereflux of the solvent for 1 hour
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated under reduced pressure
  5. customthe organic phase is then separated
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-474bc90f3d044d57abe17bead593fade
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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