Pyridinium chloride → [4-(4-Hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone

HRID 2104502Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]3[C:13](=[C:14]([C:19]([F:22])([F:20])[F:21])[CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of [4-(4-methoxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (1.3 g, 3.3 mmol) and pyridine HCl(10 g) was heated to 200° C. After 1 hr, the reaction was cooled and then diluted with 2N HCl. The acidic layer was extracted with EtOAc, dried and concentrated to give an oil which was triturated with 10% EtOAc/hexane to give a solid which was collected by filtration to give ([4-(4-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.80 g, Yield=68%); MS (ESI) m/z 394 ([M+H]+); 1H NMR (DMSO) δ 9.72 (bs, 1H), 9.08 (s, 1H), 8.31 (d, 1H, J=6.8 Hz), 8.06 (d, 1H, J=8.6 Hz), 7.80-7.75 (m, 1H), 7.62-7.60 (m, 2H), 7.58-7.54 (m, 1H), 7.38-7.35 (m, 2H), 7.13 (d, 2H, J=7.8 Hz), 6.75 (d, 2H, J=7.8 Hz);

Workup

temperaturethe reaction was cooled
extractionThe acidic layer was extracted with EtOAc
customdried
concentrationconcentrated
customto give an oil which
customwas triturated with 10% EtOAc/hexane
customto give a solid which
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-d28d0252fa934afbb311a6bb6044883a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576215B2

Reaction notes

Loading…