Hydrochloric Acid → 5-Chloro-2-[(5-fluoropyridin-3-yl)oxy]benzoic acid

HRID 1293259Notes

Reaction equation

HRID 1293259 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69418031Methyl 5-chloro-2-[(5-fluoropyridin-3-yl)oxy]benzoate

Product 1

HCID 694158495-Chloro-2-[(5-fluoropyridin-3-yl)oxy]benzoic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-chloro-2-[(5-fluoropyridin-3-yl)oxy]benzoate (80 mg, 0.28 mmol) in methanol (2 mL) was added 2 M sodium hydroxide aqueous solution (2 mL) and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was acidified with 2 M hydrochloric acid (2.5 mL). The precipitate was collected by filtration to afford 61 mg (80%) of the title compound: 1H-NMR (CDCl3) δ 8.24 (1H, br.s), 8.19 (1H, br.s), 8.07 (1H, d, J=2.6 Hz), 7.56 (1H, d, J=8.8, 2.6 Hz), 7.06 (1H, d, J=8.8 Hz), 6.98 (1H, td, J=9.4, 2.2 Hz).

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-0410c99ae4774f83acc20ad423797207
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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