Water → 3-(4-Fluorophenyl)-6-methylpicolinic acid

HRID 61004Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:15]#N)=[N:10][C:11]([CH3:14])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-:17].[Na+].[OH2:19]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:15]([OH:19])=[O:17])=[N:10][C:11]([CH3:14])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the solution of 3-(4-fluorophenyl)-6-methylpicolinonitrile (0.555 g, 2.615 mmol) in MeOH (3 mL) was added NaOH (1.1 g, 27.5 mmol) and H2O (1.8 mL). The mixture was heated at 100° C. for 8 h. The reaction was cooled to rt and acidified to pH-5. The solvent was removed in vacuo. The crude was extracted with MeOH. The solvent was removed in vacuo and the obtained acid was dried in vacuum for next step with no further purification. ESI-MS (m/z): 233 [M+1]+.

Workup

temperatureThe reaction was cooled to rt
customThe solvent was removed in vacuo
extractionThe crude was extracted with MeOH
customThe solvent was removed in vacuo
customthe obtained acid was dried in vacuum for next step with no further purification

Sources & evidence

ORD record: ord-db06a1b42d6e4a128ca34831ff6e42a1
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440982B2

Reaction notes

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