Water → N1-(3,5-difluorophenyl)-3,5-difluoro-benzene-1,2-diamine

HRID 2036614Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-(3,5-difluorophenyl)-3,5-difluoro-2-nitroaniline (1 g, 3.49 mmol) in AcOH (10.5 mL) was added iron powder (585 mg, 10.48 mmol) and the reaction mixture was heated to 100° C. for 1 h. The reaction mixture was cooled to rt and water was added. The organic layer was extracted with EtOAc and was basified by using satd. sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated in vacuo to provide N1-(3,5-difluorophenyl)-3,5-difluoro-benzene-1,2-diamine. The crude product was carried without further purification.

Workup

temperatureThe reaction mixture was cooled to rt
extractionThe organic layer was extracted with EtOAc
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f8edfff05db04284a8cf60fe69486837
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

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