Lithium hydroxide, monohydrate → 2-(3-Cyanophenyl)pyridine-3-carboxylic acid

HRID 2230781Notes

Reaction equation

HRID 2230781 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13]C)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].O.[OH-].[Li+]>CO.O>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15453754HCID 15453754, compound

Product 1

HCID 184634232-(3-Cyanophenyl)pyridine-3-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-(3′-cyanophenyl)nicotinate (1.21 g, 5.1 mmol) was partially dissolved in MeOH (40 mL), and lithium hydroxide monohydrate (234 mg dissolved in 6 mL H2O, 5.6 mmol) was added. After 20 hours, the resulting solution was diluted with water and extracted with CHCl3. The aqueous was acidified to pH 4 with 1 M HCl and extracted several times with CHCl3. Solid sodium chloride was added to the aqueous solution and the solution was extracted with 5-10% MeOH/CHCl3. The organic extracts were combined, dried over Na2SO4, filtered, and evaporated to yield a white solid (1.06 g, 93%). 1H NMR (CDCl3): δ8.85 (dd, 1H, J=5.1, J′=1.5), 8.35 (dd, 1H, J=7.6, J′=1.4), 7.84 (s, 1H), 7.75 (m, 2H), 7.55 (t, 1H, J=7.7), 7.47 (m, 1H).

Workup

  1. extractionextracted with CHCl3
  2. extractionextracted several times with CHCl3
  3. additionSolid sodium chloride was added to the aqueous solution
  4. extractionthe solution was extracted with 5-10% MeOH/CHCl3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5d4c460d1bb449eabd00c3f2a7282e4f
Source dataset
uspto-grants-2002_07
Patent number
US06426346B1

Reaction notes

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