Hydrochloric Acid → 6-Dimethylaminocarbonyl nicotinic acid

HRID 378856Notes

Reaction equation

HRID 378856 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[N:10]=[CH:9][C:8]([C:11]([O:13]C)=[O:12])=[CH:7][CH:6]=1)=[O:4].C1COCC1.[OH-].[Li+].Cl>O.C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[N:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 10703558Methyl 6-[(dimethylamino)carbonyl]-3-pyridine carboxylate

Product 1

HCID 216968616-Dimethylaminocarbonyl nicotinic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a 5° C. mixture of methyl 6-[(dimethylamino)carbonyl]-3-pyridine carboxylate (52.5 g, 0.252 mol) and THF (390 mL) was added a solution of lithium hydroxide (trihydrate, 11.6 g, 0.277 mol) in water (60 mL) over 6 minutes. After stirring for 1 h, 2 N HCl (145 mL) was added over a 15-min period. Toluene (200 mL) was added and the organic solvents were removed in vacuo. The slurry was filtered, and the solids were washed with water (2×20 mL) and dried at 75° C. in vacuo to provide 47 g (96%) of 6-[(dimethylamino)carbonyl]-3-pyridine carboxylic acid.

Workup

  1. customthe organic solvents were removed in vacuo
  2. filtrationThe slurry was filtered
  3. washthe solids were washed with water (2×20 mL)
  4. customdried at 75° C. in vacuo

Sources & evidence

ORD record
ord-2d132952391144ea8d0c60feb4679c15
Source dataset
uspto-grants-2001_10
Patent number
US06297233B1

Reaction notes

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