Isobutylene oxide → 1-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol

HRID 2277370Notes

Reaction equation

[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.[OH-].[Na+].[CH3:25][C:26]1([O:29][CH2:28]1)[CH3:27]>C1COCC1.O.CCOC(C)=O>[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:25][C:26]([CH3:28])([OH:29])[CH3:27])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)quinolin-7-ol (60 g, 0.2 mol) in THF/H2O (1 L, THF/H2O=1:1, v/v) was added NaOH (24 g, 0.6 mol) at room temperature, followed by isobutylene oxide (144 g, 2 mol). The reaction was stirred at 45° C. for 10 hours, and then diluted with EtOAc (1 L). The resulted solution was washed with 1 M NaOH aqueous solution (500 mL×4). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was washed with 500 mL of petroleum ether, and collected through filtration to give the title compound as a light yellow solid (31.6 g, 42.5%).

Workup

washThe resulted solution was washed with 1 M NaOH aqueous solution (500 mL×4)
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
washThe residue was washed with 500 mL of petroleum ether
filtrationcollected through filtration

Sources & evidence

ORD record: ord-2b0631696206404d8415e987f85b2276
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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