Hydrochloric Acid → HCID 21105756, compound

HRID 1354470Notes

Reaction equation

HRID 1354470 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][C:17]=3[N+:26]([O-:28])=[O:27])=[N:13][N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=3[N+:26]([O-:28])=[O:27])=[N:13][N:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21105769HCID 21105769, compound

Product 1

HCID 21105756HCID 21105756, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[5-(4-t-butylphenyl)-1,3,4-oxadiazol-2-yl]-3-nitrobenzoate (1.50 g), 1 M aqueous sodium hydroxide solution (7.8 ml) and tetrahydrofuran (10 ml) was heated under reflux for 30 min. After cooling, 1 M hydrochloric acid was added to acidify the reaction mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1-10:1, volume ratio) to give 4-[5-(4-t-butylphenyl)-1,3,4-oxadiazol-2-yl]-3-nitrobenzoic acid (0.600 g, yield 42%). Recrystallization from hexane-ethyl acetate gave colorless prism crystals. melting point: 233–235° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1-10:1, volume ratio)

Sources & evidence

ORD record
ord-c3b3968e273f413e80e67a6d4685dffd
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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