2-Methyl-5-(3-nitro-5-(trifluoromethyl)phenyl)-1,3,4-oxadiazole → 3-(5-Methyl-[1,3,4]oxadiazol-2-yl)-5-trifluoromethylphenylamine

HRID 1050119Notes

Reaction equation

[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([N+:17]([O-])=O)[CH:8]=2)=[N:5][N:6]=1>CO.[Pd]>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]([CH:10]=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=2)[NH2:17])=[N:5][N:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-methyl-5-(3-nitro-5-(trifluoromethyl)phenyl)-1,3,4-oxadiazole (20 g, 73.2 mmol) and Pd/C (0.779 g, 7.32 mmol) in MeOH (25 mL) was stirred for 12 h at 35 psi under H2 atmosphere at 25° C. Then the mixture was filtered and the filtrate was concentrated to give the residue which was crystallized with MeOH (15 mL) to yield a gray solid of 3-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)aniline (17 g, 66.4 mmol, 91% yield): 1H NMR (400 MHz, CD3OD) δ 7.46 (s, 1H), 7.42 (s, 1H), 7.07 (s, 1H), 2.61 (s, 3H); ES-LCMS m/z 244 (M+H).

Workup

filtrationThen the mixture was filtered
concentrationthe filtrate was concentrated
customto give the residue which
customwas crystallized with MeOH (15 mL)

Sources & evidence

ORD record: ord-960050920e3540a2b60e2248f76fb1a7
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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