Hydrochloric Acid → 6-Methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid

HRID 1802158Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:17]([O:19]C)=[O:18])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.O.[OH-].[Li+].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of methyl 6-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate (182 mg, 681 μmol) and lithium hydroxide monohydrate (114 mg, 2.72 mmol) in tetrahydrofurane (10 ml) and water (2 ml) is stirred for 4 hours at 25° C. The mixture is diluted with ethyl acetate, acidified to pH=0 with hydrochloric acid 37% and washed with water and brine. The organic layer is dried with magnesium sulfate and the solvent is evaporated to dryness affording 6-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid (223 mg, 129%) as a light yellow solid. mp.: 228-233° C. MS: m/z=254.2 (M+H+).

Workup

washwashed with water and brine
dry with materialThe organic layer is dried with magnesium sulfate
customthe solvent is evaporated to dryness

Sources & evidence

ORD record: ord-be445abae0b9453390db38787ba220ce
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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