1,3-Bis(3-nitrophenoxy)-5-trifluoromethylbenzene → 1,3-Bis(3-aminophenoxy)-5-trifluoromethylbenzene

HRID 1603981Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[O:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=2)[CH:9]=1)([O-])=O.[H][H]>[Pd].COCCO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[O:7][C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[C:10]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=2)[CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Into a reducing device equipped with a thermometer, a reflux condenser and an agitator were charged 55 g of 1,3-bis(3-nitrophenoxy)-5-trifluoromethylbenzene (0.131 mol), 150 g of methyl cellosolve and 5 g of 5%-Pd/C (50% of water content), and the mixture was reacted at 70 to 80° C. for 4 hours in an atmosphere of hydrogen. At the end of the reaction, the catalyst was filtered out and the filtrate was heated to 90° C., to which 140 g of water was added. The mixture was cooled to room temperature to crystallize the desired product, which was filtered and dried under a reduced pressure to give 1,3-bis(3-aminophenoxy)-5-trifluoromethylbenzene as a white solid; Melting point: 98.0 to 98.6° C., Yield: 41 g (87%).

Workup

customInto a reducing device equipped with a thermometer, a reflux condenser
customAt the end of the reaction
filtrationthe catalyst was filtered out
additionwas added
temperatureThe mixture was cooled to room temperature
customto crystallize the desired product, which
filtrationwas filtered
customdried under a reduced pressure

Sources & evidence

ORD record: ord-079a5759b51e434d8cf13e56566184af
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990261

Reaction notes

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