Hydrochloric Acid → 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid

HRID 58040Notes

Reaction equation

HRID 58040 reaction equation
[CH3:1][C:2]1[N:7]=C(C#N)[CH:5]=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2.[OH-:23].[Na+].Cl.[CH3:26][CH2:27][OH:28]>>[CH3:1][C:2]1[N:7]=[C:26]([C:27]([OH:23])=[O:28])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 897829316-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile

Product 1

HCID 897833556-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acidYield 89%

Procedure

To 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile (1.7 g, 5.62 mmol) in EtOH (20 mL) was added sodium hydroxide (14.06 mL, 28.1 mmol) and the resulting mixture was stirred for 16 hours at reflux. The mixture was subsequently cooled to room temperature and acidified with concentrated HCl. Volatiles were evaporated and the residue purified by CombiFlash® chromatography (5-40% MeOH in DCM over 120 minutes). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a white solid (1.6 g, 89%). ESI-MS m/z [M+H]+ calc'd for C15H10F3N3O2, 322.1. found 322.06.

Workup

  1. temperatureat reflux
  2. customVolatiles were evaporated
  3. customthe residue purified by CombiFlash® chromatography (5-40% MeOH in DCM over 120 minutes)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67116a1f1f614286a64f0da071cfc36a
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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