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

Temperature

73 °C

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%).

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

ORD record

ord-1e9fc707e9e2418186508247857643ad

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133162B2