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

HRID 2277396Notes

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

Participants

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

customquenched with H2O (30 mL)
customThe organic solvent was removed in vacuo
additionthe residue was diluted with DCM (100 mL)
customThe organic phase was separated
dry with materialdried over Na2SO4
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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