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

HRID 2277370
Notes
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Reaction equation

HRID 2277370 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11208Isobutylene oxideHCID 14798Sodium HydroxideHCID 1357421754-(2-Fluoro-4-nitrophenoxy)quinolin-7-ol

Product 1

HCID 681940281-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-olYield 42.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 21881883
Oxolane--water (1/1)
Solvent
2×

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

  1. washThe resulted solution was washed with 1 M NaOH aqueous solution (500 mL×4)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with 500 mL of petroleum ether
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes