Acetic Acid → N-(3'-Amino-6-methylbiphenyl-3-yl)-3-fluoro-5-(trifluoromethyl)benzamide

HRID 1894874Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)[C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:6].C(O)C.C(O)(=O)C>[Fe].CCOC(C)=O>[NH2:21][C:17]1[CH:16]=[C:15]([C:10]2[C:11]([CH3:14])=[CH:12][CH:13]=[C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:24]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:26]=[C:2]([F:1])[CH:3]=3)[CH:9]=2)[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 92 °C

Procedure

To 3-fluoro-N-(6-methyl-3′-nitrobiphenyl-3-yl)-5-(trifluoromethyl)benzamide (4.09 g, 9.78 mmol) was added ethanol (93.2 mL) followed by iron (3.0 g, 54 mmol) and acetic acid (9.32 mL, 164 mmol). The solution was heated at 92° C. for 2 h using the rotovap motor/heating bath. To the reaction mixture was added EtOAc and the mixture was then filtered and was concentrated in vacuo. The residue was used in the next reaction without purification. MS (EI) m/z=389 (M+H).

Workup

filtrationthe mixture was then filtered
concentrationwas concentrated in vacuo
customThe residue was used in the next reaction without purification

Sources & evidence

ORD record: ord-072e2b382b0f4eff9eb60ef3eab5a66d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513270B2

Reaction notes

Loading…