Sodium Hydroxide → 2-Bromo[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid

HRID 60131Notes

Reaction equation

HRID 60131 reaction equation
[OH-].[Na+].[Br:3][C:4]1[N:16]=[C:7]2[CH:8]=[C:9]([C:12]([O:14]C)=[O:13])[CH:10]=[CH:11][N:6]2[N:5]=1>CO>[Br:3][C:4]1[N:16]=[C:7]2[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=[CH:11][N:6]2[N:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90383439Methyl 2-bromo-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate

Product 1

HCID 838249652-Bromo[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 N sodium hydroxide aqueous solution (150 ml) was added to a methanol (150 ml) suspension of the methyl 2-bromo-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate (10 g) obtained in (Example 3.15) <Step 2>, and the obtained mixture was then stirred for 30 minutes. Thereafter, about half of the solvent was distilled away under reduced pressure, and the residue was then adjusted to pH 4 by addition of 3 N hydrochloric acid (50 ml). The precipitated solid was collected by filtration, and was then successively washed with water (50 ml) and methyl tert-butyl ether (20 ml). The obtained solid was subjected to azeotropy with toluene to obtain the title compound (9.0 g) in the form of a white solid.

Workup

  1. customobtained in (Example 3.15) <Step 2>
  2. distillationThereafter, about half of the solvent was distilled away under reduced pressure
  3. additionthe residue was then adjusted to pH 4 by addition of 3 N hydrochloric acid (50 ml)
  4. filtrationThe precipitated solid was collected by filtration
  5. washwas then successively washed with water (50 ml) and methyl tert-butyl ether (20 ml)

Sources & evidence

ORD record
ord-17e20c9d19c54de9b6112be5854ce164
Source dataset
uspto-grants-2016_09
Patent number
US09440970B2

Reaction notes

Loading…