Methane → 5-Amino-2'-fluoro-6-hydroxybiphenyl-3-carbonitrile

HRID 2093630Notes

Reaction equation

C.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]([OH:15])=[C:13]([N+:16]([O-])=O)[CH:12]=[C:11]([C:19]#[N:20])[CH:10]=1.NN>CO.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[NH2:16][C:13]1[CH:12]=[C:11]([C:19]#[N:20])[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[F:2])[C:14]=1[OH:15]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of charcoal (283 mg) in 25 ml of methanol was added iron (III) chloride hexahydrate (35 mg), and 2′-fluoro-6-hydroxy-5-nitrobiphenyl-3-carbonitrile (668 mg). The resultant green mixture was heated under nitrogen at 70° C. for 10 min. Hydrazine (403 μl) was added slowly, and the mixture was stirred for 2 h at 70° C. The mixture was then cooled to room temperature and filtered through a plug of Celite. The eluent was concentrated in vacuo to provide the title compound (543 mg, 92%). Mass spectrum (ESI) 229.1 (M+1).

Workup

temperatureThe mixture was then cooled to room temperature
filtrationfiltered through a plug of Celite
concentrationThe eluent was concentrated in vacuo

Sources & evidence

ORD record: ord-a866facd77214c38ad7fb90eea6260b2
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445480B2

Reaction notes

Loading…