Hydrochloric Acid → 2-Acetamido-6-methylisonicotinic acid

HRID 623555Notes

Reaction equation

HRID 623555 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH3:15])[N:14]=1)[C:8]([O:10]C)=[O:9])(=[O:3])[CH3:2].[OH-].[Na+].Cl>O1CCCC1>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH3:15])[N:14]=1)[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67510177Methyl 2-acetamido-6-methylisonicotinate

Product 1

HCID 675102662-Acetamido-6-methylisonicotinic acidYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-acetamido-6-methylisonicotinate (1.99 g, 9.56 mmol, Step-1), 0.5M aqueous sodium hydroxide solution (20 mL, 10.0 mmol) and tetrahydrofuran (64 mL) is stirred at room temperature for 2.5 hours. The mixture is acidified by 2M hydrochloric acid and the organic solvent is removed by evaporation. The precipitate is collected by filtration and washed with diisopropyl ether to give 0.81 g (44% yield) of the title compound as a slight yellow solid.

Workup

  1. customthe organic solvent is removed by evaporation
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-173d19aa8d4e405db7efbab8af6868b7
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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