Sodium Hydroxide → 6-Chloro-2-methyl-3-(1H-1,2,3-triazol-4-yl)pyridine

HRID 385973Notes

Reaction equation

HRID 385973 reaction equation
C(OC[N:9]1[CH:13]=[C:12]([C:14]2[C:15]([CH3:21])=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[N:11]=[N:10]1)(=O)C(C)(C)C.[OH-].[Na+]>CO>[Cl:20][C:17]1[N:16]=[C:15]([CH3:21])[C:14]([C:12]2[N:11]=[N:10][NH:9][CH:13]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59525806[4-(6-Chloro-2-methylpyridin-3-yl)-1H-1,2,3-triazol-1-yl]methyl pivalate

Product 1

HCID 1784328616-Chloro-2-methyl-3-(1H-1,2,3-triazol-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[4-(6-Chloro-2-methylpyridin-3-yl)-1H-1,2,3-triazol-1-yl]methyl pivalate (350 mg, 0.96 mmol) was taken up in methanol (3.9 ml) at room temperature. Aqueous sodium hydroxide (1.0M, 4.8 ml, 4.8 mmol) was added, and the mixture was allowed to react for 2 hours. The reaction was then extracted three times with diethyl ether. The combined organic fractions were washed with water. The combined aqueous layers were adjusted to pH 7.0 via dropwise addition of 6 M aqueous hydrochloric acid. The neutralized mixture was saturated with solid sodium chloride and extracted three times with ethyl acetate. All the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound.

Workup

  1. customto react for 2 hours
  2. extractionThe reaction was then extracted three times with diethyl ether
  3. washThe combined organic fractions were washed with water
  4. additionThe combined aqueous layers were adjusted to pH 7.0 via dropwise addition of 6 M aqueous hydrochloric acid
  5. extractionextracted three times with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d56a19a36c594441bb69022950a35546
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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