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

HRID 77702Notes

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-748b9c4763c043f9bcfedbd17eb6c2f7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841318B2

Reaction notes

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