Lithium Hydroxide → 6-Phenylnicotinic acid

HRID 1177965Notes

Reaction equation

HRID 1177965 reaction equation
[Li+].[OH-].C([O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][CH:8]=1)C>C1COCC1.CO.O>[C:13]1([C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:19])=[O:5])=[CH:8][N:9]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11096332Ethyl 6-phenylnicotinate

Product 1

HCID 1201186-Phenylnicotinic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (38 mg, 0.93 mmol) was added to a stirred solution of 6-phenyl-nicotinic acid ethyl ester (140 mg, 0.62 mmol) in THF:MeOH:H2O (3:1:1, 2.8 mL), and the resulting mixture was stirred at room temperature overnight. The methanol and THF were evaporated from the reaction mixture, which was then diluted with water (2 mL), acidified with citric acid solution and the product was extracted with EtOAc. The organic layer was washed with saturated brine solution, dried over Na2SO4 and concentrated in vacuo to afford 100 mg (81.9% yield) of 6-phenyl-nicotinic acid (100 mg). LCMS purity: 98.1%.

Workup

  1. customThe methanol and THF were evaporated from the reaction mixture, which
  2. additionwas then diluted with water (2 mL)
  3. extractionthe product was extracted with EtOAc
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-253107f113c64193abd02411e553e848
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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