Sodium Hydroxide → 2-Chloro-4-fluoro-5-(pyridin-2-yl)benzoic acid

HRID 522136Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of methyl 2-chloro-4-fluoro-5-(pyridin-2-yl)benzoate (Preparation 40A, 37.6 g, 142 mmol) in methanol (300 mL) was added aqueous sodium hydroxide solution (300 mL, 2 M). The reaction mixture was stirred at 40° C. for 2 hours. The mixture was filtered and the filtrate acidified to pH 6-7 with aqueous HCl solution (300 mL, 2 M). The resulting solid was collected by filtration, washed with water (20 mL) and dried under vacuum over potassium hydroxide at 50° C. for 48 h to afford the title compound as a white solid (36.2 g, 100%).

Workup

filtrationThe mixture was filtered
filtrationThe resulting solid was collected by filtration
washwashed with water (20 mL)
dry with materialdried under vacuum over potassium hydroxide at 50° C. for 48 h

Sources & evidence

ORD record: ord-ff2199aa3b3649daa9211b354627bcc3
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328096B2

Reaction notes

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