Hydrochloric Acid → 2-Methyl-6-(1h-1,2,4-triazol-1-yl)pyridin-3-ol

HRID 1931575Notes

Reaction equation

HRID 1931575 reaction equation
[CH3:1][C:2]1[C:7]([O:8]C(=O)C)=[CH:6][CH:5]=[C:4]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[N:3]=1.[OH-].[Na+].Cl>>[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[N:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669152932-Methyl-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl acetate

Product 1

HCID 579650072-Methyl-6-(1h-1,2,4-triazol-1-yl)pyridin-3-olYield 95.6%

Conditions

Temperature
0 °C

Procedure

Acetic acid 2-methyl-6-[1,2,4]triazol-1-yl-pyridin-3-yl ester (125 mg, 0.57 mmol) was added to 2 M aqueous sodium hydroxide solution (1.6 mL) at 0° C. to give a slurry, and the mixture was stirred at 0° C. for 20 min and then at room temperature for 3 h. 2 M Aqueous hydrochloric acid was added to bring the pH to 6, and the mixture was extracted four times with ethyl acetate. The organic layers were combined and the solvent was evaporated to dryness to give 2-methyl-6-[1,2,4]triazol-1-yl-pyridin-3-ol (96 mg, 95%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ 2.36 (s, 3H), 7.33 (d, 1H, J=8.7 Hz), 7.51 (d, 1H, J=8.5 Hz), 8.18 (s, 1H), 9.12 (s, 1H), 10.19 (br s, 1H).

Workup

  1. customto give a slurry
  2. waitat room temperature for 3 h
  3. extractionthe mixture was extracted four times with ethyl acetate
  4. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-6f5d41db9a914a05b48ac577ec265557
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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