Hydrochloric Acid → 2-(Ethylcarbamoyl)isonicotinic acid

HRID 623568Notes

Reaction equation

HRID 623568 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][N:15]=1)[C:9]([O:11]C)=[O:10])=[O:5])[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([NH:3][C:4]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][N:15]=1)[C:9]([OH:11])=[O:10])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67509052Methyl 2-(ethylcarbamoyl)isonicotinate

Product 1

HCID 675093812-(Ethylcarbamoyl)isonicotinic acidYield 101.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(ethylcarbamoyl)isonicotinate (520 mg, 2.50 mmol, Step-1), 2M aqueous sodium hydroxide solution (2.5 mL), and methanol (6 mL) is stirred at room temperature for 3 hours. After addition of 2M hydrochloric acid (2.5 mL), the solvent is removed by evaporation. The residue is suspended in THF (20 mL), and the mixture is filtered through a pad of Celite. The filtrate is concentrated in vacuo to give 491 mg (quantitative yield) of the title compound as a white solid.

Workup

  1. customthe solvent is removed by evaporation
  2. filtrationthe mixture is filtered through a pad of Celite
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-b8a757b94a96408db3df704dd6873bf1
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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