Sodium Hydroxide → HCID 21964226, compound

HRID 2212335Notes

Reaction equation

HRID 2212335 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9](=[O:25])[CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17]C(OC(C)(C)C)=O)[CH:12]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-].[Na+]>Cl>[NH2:17][C:13]1[CH:12]=[C:11]([CH2:10][C:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[O:25])[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21964243HCID 21964243, compound

Product 1

HCID 21964226HCID 21964226, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

2N-hydrochloric acid (50 mL) was added to 1-(3,5-dimethylphenyl)-2-(2-tert-butoxycarbonylamino-4-pyridyl)ethanone (12 g, 36 mmol) and the mixture was stirred at 100° C. for 1 hour. After the reaction mixture was cooled to room temperature, an 8N aqueous solution of sodium hydroxide (15 mL) was added and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized from ethyl acetate to obtain 6.8 g of the title compound (28 mmol, yield 77%).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-621053cb11af4a2e96fba4ca201e5cee
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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