Acetic Acid → 4'-Formyl-3'-(trifluoromethyl)-1,1'-biphenyl-3-carboxamide

HRID 471865Notes

Reaction equation

[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([NH2:20])=[O:19])[CH:13]=2)=[CH:8][C:7]=1[C:21]([F:24])([F:23])[F:22].CC(O)=O.C([O-])(O)=O.[Na+]>O>[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([NH2:20])=[O:19])[CH:13]=2)=[CH:8][C:7]=1[C:21]([F:22])([F:23])[F:24])=[O:1]

Participants

Conditions

Temperature: 65 °C

Procedure

4′-(1,3-Dioxolan-2-yl)-3′-(trifluoromethyl)-1,1′-biphenyl-3-carboxamide (0.177 g; 0.525 mmol) was added to a solution of HOAc (4 mL) and water (1 mL) and the mixture was stirred at 65° C. in a sealed vial for 1 h. Upon cooling, the mixture was poured into satd NaHCO3 and extracted with EtOAc (×3). Combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound, which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.55 (br. s., 1H), 7.64 (t, J=7.76 Hz, 1H), 7.98 (ddd, J=7.98, 1.38, 1.16 Hz, 1H), 8.02 (ddd, J=7.76, 1.87, 1.07 Hz, 1H), 8.18-8.26 (m, 3H), 8.29 (dd, J=8.03, 1.78 Hz, 1H), 8.31 (t, J=1.69 Hz, 1H), 10.31 (q, J=1.96 Hz, 1H)

Workup

temperatureUpon cooling
extractionextracted with EtOAc (×3)
washCombined organics were washed (water, brine)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-80732557673f48d9a9da5b9517162e27
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633175B2

Reaction notes

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