Hydrochloric Acid → 6-(Dimethylamino)-5-methyl-3-pyridinecarboxylic acid

HRID 502424Notes

Reaction equation

HRID 502424 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[C:10]([CH3:11])=[CH:9]C(C#N)=[CH:5][N:4]=1.[OH-].[Na+].Cl.C1C[O:19]CC1.[CH2:21]([OH:23])[CH3:22]>>[CH3:1][N:2]([CH3:12])[C:3]1[C:10]([CH3:11])=[CH:9][C:22]([C:21]([OH:19])=[O:23])=[CH:5][N:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21873804Tetrahydrofuran ethanolHCID 68455945HCID 68455945, compound

Product 1

HCID 684549596-(Dimethylamino)-5-methyl-3-pyridinecarboxylic acid

Procedure

The above prepared 6-dimethylamino-5-methyl-nicotinonitrile (0.435 g, 2.70 mmol) was dissolved in 13.6 ml of THF/ethanol=1/1 and treated with 6.75 ml of 2N NaOH (5 eq.). The mixture was refluxed for 30 h; aliquots were taken from time to time and analyzed by MS to follow the disappearance of the amide intermediate. After cooling down to room temperature, the pH was adjusted with HCl to 3. Careful evaporation of the solvents and drying under HV left 1.45 g of the title acid as white solid, contaminated with NaCl, which was used as such for the next step.

Workup

  1. temperatureThe mixture was refluxed for 30 h
  2. customCareful evaporation of the solvents
  3. customdrying under HV
  4. waitleft 1.45 g of the title acid as white solid

Sources & evidence

ORD record
ord-129956e00932491ca0f2fc902c01cffa
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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