Sodium Hydroxide → SC-68376

HRID 1595199Notes

Reaction equation

HRID 1595199 reaction equation
[C:1]([NH:4][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=[O:7])(=O)[CH3:2].[OH-].[Na+]>OS(O)(=O)=O>[CH3:2][C:1]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21704188HCID 21704188, compound

Product 1

HCID 5174SC-68376

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-acetamido-2-phenyl-1-(4-pyridyl)ethanone (0.101 g, 0.397 mmol) in conc. H2SO4 (1 mL) was heated at 100° C. for 18 h. After cooling, the mixture was poured onto ice and neutralized with 2.5N NaOH. The aqueous mixture was extracted with CH2Cl2 and the combined organic extracts were washed with sat'd NaCl and dried over MgSO4. Evaporation of solvent gave an oil which was purified by flash chromatography, eluting with 0-2% MeOH/CHCl3. The title compound was obtained as a gold oil (3.0 mg): MS(DCI/NH3) (m/z): 237 (M++H).

Workup

  1. temperatureAfter cooling
  2. extractionThe aqueous mixture was extracted with CH2Cl2
  3. washthe combined organic extracts were washed with sat'd NaCl
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent
  6. customgave an oil which
  7. customwas purified by flash chromatography
  8. washeluting with 0-2% MeOH/CHCl3

Sources & evidence

ORD record
ord-039648bbe9eb4cb9ad50d3d08afc3a21
Source dataset
uspto-grants-2001_09
Patent number
US06288062B1

Reaction notes

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