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Aluminium lithium hydride → 2-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-1-ol

HRID 2277396
Notes
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Reaction equation

HRID 2277396 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]([CH3:22])([CH3:21])[C:17](OC)=[O:18])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]([CH3:22])([CH3:21])[CH2:17][OH:18])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68193885Methyl 2-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoate

Product 1

HCID 681939022-((4-(2-Fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoate (3 g, 7.5 mmol) in THF (25 mL) was added LiAlH4 (0.34 g, 9 mmol) in portions at 0° C. The reaction was stirred at 0° C. for 4 hours and then quenched with H2O (30 mL). The organic solvent was removed in vacuo and the residue was diluted with DCM (100 mL). The organic phase was separated, dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a yellow solid (0.95 g, 34.1%).

Workup

  1. customquenched with H2O (30 mL)
  2. customThe organic solvent was removed in vacuo
  3. additionthe residue was diluted with DCM (100 mL)
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e461d50a18e4ede887258579471dd48
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