Sodium Hydroxide → 1-(3,4-difluorophenyl)-1H-1,2,4-triazole-3-carboxylic acid

HRID 1755235Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[N:12][C:11]([C:14]([O:16]CC)=[O:15])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+]>CCO.O>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[N:12][C:11]([C:14]([OH:16])=[O:15])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 1-(3,4-difluorophenyl)-1H-1,2,4-triazole-3-carboxylate (0.30 g, 1.2 mmol, 1 eq) in 5 mL of EtOH/H2O (1.5:1) was added NaOH (0.095 g, 2.4 mmol, 2 eq). The reaction mixture was heated at 50° C. for 1 h then quenched with 0.20 mL of cone. HCl. The contents were filtered and washed with EtOAc then with MeOH and the MeOH filtrate was dried with Na2SO4 and concentrated in vacuo to afford 1-(3,4-difluorophenyl)-1H-1,2,4-triazole-3-carboxylic acid (0.22 g, 0.98 mmol, 84%).

Workup

customthen quenched with 0.20 mL of cone
filtrationThe contents were filtered
washwashed with EtOAc
dry with materialwith MeOH and the MeOH filtrate was dried with Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9fa712c2f70249e69a6d02619310dcb7
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169261B2

Reaction notes

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