Hydrogen Bromide → Elq-300

HRID 1908996Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[C:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=[CH:17][CH:16]=1)=[C:5]2[O:33]CC.Br>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7]([CH3:14])=[C:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:30])([F:32])[F:31])=[CH:24][CH:23]=3)=[CH:17][CH:16]=1)[C:5]2=[O:33]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 6-chloro-4-ethoxy-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinoline (1.16 g, 2.30 mmol) in acetic acid (10 ml) was added a 50% aqueous hydrobromic acid solution (5 ml). The reaction mixture was stirred 24 hours at 90° C., cooled and concentrated in vacuo. The resulting residue was resuspended in water, neutralized with 2 N NaOH and filtered. The collected solid was triturated with dichloromethane and filtered to provide 923 mg 6-chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolin-4(1H)-one (84% yield) as a white powder. 1H NMR (400 MHz, CDCl3) δ 11.97 (s, 1H), 8.05 (s, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.29 (d, J=8.3 Hz, 2H), 7.17 (d, J=8.3 Hz, 2H), 7.12 (s, 1H), 7.08 (d, J=8.7 Hz, 2H), 3.97 (s, 3H), 2.26 (s, 3H). HRMS (EI+) m/z for C24H17ClF3NO4: calculated 475.0798, found 475.0801.

Workup

temperaturecooled
concentrationconcentrated in vacuo
filtrationfiltered
customThe collected solid was triturated with dichloromethane
filtrationfiltered

Sources & evidence

ORD record: ord-a04ec85dcab94145bc7d71a940ac220d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598354B2

Reaction notes

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