Citric Acid → 5-{[6-(5-Methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrobenzoic acid

HRID 2080677Notes

Reaction equation

HRID 2080677 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[N:14]=[CH:13][C:12]([O:15][C:16]3[CH:17]=[CH:18][C:19]([N+:26]([O-:28])=[O:27])=[C:20]([CH:25]=3)[C:21]([O:23]C)=[O:22])=[CH:11][CH:10]=2)[N:5]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[N:14]=[CH:13][C:12]([O:15][C:16]3[CH:17]=[CH:18][C:19]([N+:26]([O-:28])=[O:27])=[C:20]([CH:25]=3)[C:21]([OH:23])=[O:22])=[CH:11][CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 67110584Methyl 5-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrobenzoate

Product 1

HCID 671105555-{[6-(5-Methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrobenzoic acidYield 59.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.96 ml of aqueous 5 N sodium hydroxide solution was added to a solution of 700 mg of methyl 5-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrobenzoate in 5 ml of methanol and 5 ml of tetrahydrofuran, and stirred at room temperature for 2.5 hours. Aqueous 10% citric acid solution was added to neutralize it, then extracted with ethyl acetate, and the organic layer was dried, and the solvent was evaporated away under reduced pressure to obtain 399 mg of 5-{[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]oxy}-2-nitrobenzoic acid as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic layer was dried
  3. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-a94d843148a146e5a4bd447984db355f
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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