Sodium Hydroxide → HCID 2784745, compound

HRID 34081Notes

Reaction equation

HRID 34081 reaction equation
C[C:2](C)(C)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[CH3:12])=[O:4].[OH-].[Na+]>Cl>[CH3:12][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13154240N-(3-Methylpyridin-4-yl)pivalamide

Product 1

HCID 2784745HCID 2784745, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

To 17.5 g of 2,2-dimethyl-N-(3-methylpyridin-4-yl)propionamide, 70 mL of 5N hydrochloric acid aqueous solution was added and stirred at 90° C. for a day. Under ice cooling, the solution was neutralized with 5N sodium hydroxide aqueous solution, and the solvent was evaporated. The crystals were washed with a mixed solution of dichloromethane:methanol=10:1, and the solvent of filtrate was evaporated. To a solution of the resultant crude product in 100 mL of pyridine, 17.2 mL of acetic anhydride was added at room temperature and stirred at this temperature for 6 hours. The solvent was evaporated, and the residue was purified and separated by NH silica gel column chromatography (ethyl acetate:n-hexane=1:1), to afford 12.1 g of the title compound as colorless crystals.

Workup

  1. customthe solvent was evaporated
  2. washThe crystals were washed with a mixed solution of dichloromethane
  3. custommethanol=10:1, and the solvent of filtrate was evaporated
  4. additionTo a solution of the resultant crude product in 100 mL of pyridine, 17.2 mL of acetic anhydride was added at room temperature
  5. stirringstirred at this temperature for 6 hours
  6. customThe solvent was evaporated
  7. customthe residue was purified
  8. customseparated by NH silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-2a3ad4d2439c48c8a1379b2121362334
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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