Methanol → 3-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 243874Notes

Reaction equation

[CH3:1][C:2]1[C:3]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#N.[OH-:15].[Na+].C[OH:18]>O>[CH3:1][C:2]1[C:3]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([OH:18])=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-methyl-2-(2H-1,2,3-triazol-2-yl)benzonitrile (1.4 g, 7.82 mmol) in MeOH (15 mL) was added a 4N aqueous solution of NaOH (10 mL). The resulting mixture was heated to 90° C. After 15 h the reaction mixture was cooled to ambient temperature then diluted with water (50 mL). The aqueous layer was acidified to pH2 and extracted with EtOAc (50 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAc/DCM) to yield the title compound (1.3 g, 78%). 1H NMR (500 MHz, CDCl3): 7.90 (d, J=7.7, Hz, 1H), 7.83 (s, 2H), 7.57-7.53 (m, 1H), 7.49 (dd, J=9.7, 5.8 Hz, 1H), 2.10 (s, 3H).

Workup

temperatureAfter 15 h the reaction mixture was cooled to ambient temperature
extractionextracted with EtOAc (50 mL) three times
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAc/DCM)

Sources & evidence

ORD record: ord-e67d3fe552064142894bba07d09df3fb
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653263B2

Reaction notes

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