3-(4-nitrophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole → 4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)aniline

HRID 520217Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To 3-(4-nitrophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole (22.0 g, 65.8 mmol) in acetic acid (132 mL) and water (110 mL) was added iron powder. The reaction was heated to 90° C. for 18 hours. The reaction was cooled to room temperature and filtered through Celite® followed by an ethyl acetate wash. The organic layer was separated and concentrated. Purification by flash column chromatography using 0-50% ethyl acetate/petroleum ether as eluent provided the title compound as a light yellow solid (15.6 g, 74%): 1H NMR (300 MHz, CDCl3) δ 8.00 (d, J=1.0 Hz, 1H), 7.68-6.92 (m, 6H), 6.29-5.93 (m, 2H), 3.27 (bs, 2H); ESIMS m/z 305 ([M+H]+).

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered through Celite®
washwash
customThe organic layer was separated
concentrationconcentrated
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-63fc97e5fd3d44d39a240323a87e0b52
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326516B2

Reaction notes

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