(R)-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol → (R)-1-((4-(4-aminophenoxy)quinolin-7-yl)oxy)propan-2-ol

HRID 2277391Notes

Reaction equation

[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][C@H:21]([OH:23])[CH3:22])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.C(O[K])=O>C1COCC1.O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][C@H:21]([OH:23])[CH3:22])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 73 °C

Procedure

To a suspension of (R)-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol (3.6 g, 10.6 mmol) and HCOOK (6.2 g, 74.1 mmol) in THF/H2O (33 mL/11 mL) was added a catalytic amount of 10% Pd/C (33 mg). After stirring at 73° C. for 5 hours, the reaction mixture was cooled to room temperature. The mixture was filtered through a celite pad and the filter cake was washed with DCM (50 mL). The organic phase was separated, dried over Na2SO4, and concentrated in vacuo. The residue was purified by a column chromatography on silica gel (EtOAc/PE=1:1) to give the title compound as a yellow solid (2.5 g, 76.2%).

Workup

temperaturethe reaction mixture was cooled to room temperature
filtrationThe mixture was filtered through a celite pad
washthe filter cake was washed with DCM (50 mL)
customThe organic phase was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a column chromatography on silica gel (EtOAc/PE=1:1)

Sources & evidence

ORD record: ord-1e9fc707e9e2418186508247857643ad
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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