Hydrochloric Acid → 3-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine

HRID 2421103Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[O:13][C:14]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:19][O:20][C:21]=2[CH3:22])=[N:15][N:16]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[O:13][C:14]([C:17]2[C:18]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:19][O:20][C:21]=2[CH3:22])=[N:15][N:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 2-(2-methoxy-4-nitro-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole (200 mg, 0.53 mmol) in ethanol (2 mL) was added iron powder (148 mg, 2.64 mmol) and aqueous HCl (1 M, 0.53 mL, 0.53 mmol). The reaction mixture was stirred for 2 h at 90° C., cooled to ambient temperature and poured onto an aqueous solution of sodium carbonate (saturated, 20 mL) and ethyl acetate (20 mL) and then stirred for 1 h. Filtration over Hyflo® was followed by washing of the Hyflo® with ethyl acetate. The aqueous phase was extracted with ethyl acetate (20 mL). Drying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100) afforded the title compound (80 mg, 43%) as a white solid. MS: m/e=349.2 [M+H]+.

Workup

temperaturecooled to ambient temperature
stirringstirred for 1 h
filtrationFiltration over Hyflo®
washby washing of the Hyflo® with ethyl acetate
extractionThe aqueous phase was extracted with ethyl acetate (20 mL)
dry with materialDrying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=50:50 to 0:100)

Sources & evidence

ORD record: ord-dd8df703e7134904804081992952983b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956074B2

Reaction notes

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