Sodium Hydroxide → HCID 43839863, compound

HRID 623551Notes

Reaction equation

HRID 623551 reaction equation
[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][N:15]=1)[C:9]([O:11]C)=[O:10])(=[O:4])[CH2:2][CH3:3].[OH-].[Na+]>CO>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][N:15]=1)[C:9]([OH:11])=[O:10])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 675083644-Pyridinecarboxylic acid, 2-[(1-oxopropyl)amino]-, methyl ester

Product 1

HCID 43839863HCID 43839863, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 2-propionamidoisonicotinate (1.07 g, 5.15 mmol), 2M aqueous sodium hydroxide solution (5 mL) and methanol (25 mL) is stirred at 50° C. for 2 hours. After removal of the methanol by evaporation, the solution is acidified by 2M hydrochloric acid and extracted with ethyl acetate. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is crystallized from tetrahydrofuran and n-hexane to give 0.76 g (76% yield) of the title compound as a white solid.

Workup

  1. customAfter removal of the methanol
  2. customby evaporation
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is crystallized from tetrahydrofuran and n-hexane

Sources & evidence

ORD record
ord-d9ecda34b2eb4c02bcad2d4e3b16c273
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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