Sodium Hydroxide → Isonicotinic Acid

HRID 2204182Notes

Reaction equation

HRID 2204182 reaction equation
COCCO[C:6]1[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][N:7]=1.[OH-].[Na+]>O1CCOCC1>[N:7]1[CH:8]=[CH:9][C:10]([C:12]([OH:14])=[O:13])=[CH:11][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58551310Methyl 2-(2-methoxyethoxy)pyridine-4-carboxylate

Product 1

HCID 5922Isonicotinic AcidYield 139.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 2-(2-methoxyethoxy)pyridine-4-carboxylate (562 mg, 2.66 mmol), dioxane (6 mL) and NaOH (7.1 mL of 1 M, 7.1 mmol) were combined and the mixture was heated at 80° C. for 50 min. The solvent was evaporated under reduced pressure and the residue was dissolved in water before it was washed with EtOAc (3×). The aqueous layer was acidified with 1N HCl and was washed with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure to yield 242-methoxyethoxy)pyridine-4-carboxylic acid (457 mg, 87%) as a white solid. ESI-MS m/z calc. 197.2, found 198.3 (M+1)+; Retention time: 0.66 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.64 (s, 1H), 8.32 (d, J=5.2 Hz, 1H), 7.39 (d, J=5.2 Hz, 1H), 7.18 (s, 1H), 4.51-4.27 (m, 2H), 3.78-3.54 (m, 2H), 3.30 (s, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water before it
  3. washwas washed with EtOAc (3×)
  4. washwas washed with EtOAc (3×)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-20fb1f4214d84126b5f817c556ec2eb6
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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