HCID 22934563, compound → HCID 22934553, compound

HRID 1354475Notes

Reaction equation

HRID 1354475 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=3[N+:24]([O-])=O)=[N:11][N:10]=2)=[CH:5][CH:4]=1>[Pd].O1CCCC1>[NH2:24][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:14]=1[C:12]1[O:13][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:28])([F:27])[F:1])=[CH:4][CH:5]=2)=[N:10][N:11]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 1

HCID 22934563HCID 22934563, compound

Product 1

HCID 22934553HCID 22934553, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]-3-nitrobenzoate (0.500 g), 5% palladium on carbon (0.500 g) and tetrahydrofuran (10 ml) was stirred under a hydrogen atmosphere at room temperature and normal pressure for 30 min. Palladium on carbon was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, volume ratio) to give methyl 3-amino-4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoate (0.36 g, yield 77%). Recrystallization from hexane-ethyl acetate gave yellow prism crystals. melting point: 237–238° C.

Workup

  1. filtrationPalladium on carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, volume ratio)

Sources & evidence

ORD record
ord-e220afbf68c845bfbcd2574c17c7b080
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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