2-Methyl-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol → 1-((4-(4-Aminophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol

Temperature

45 °C

To a solution of 2-methyl-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol (2.8 g, 7.9 mmol) and HCOOK (4.6 g, 55.3 mmol) in water (4 mL) and THF (12 mL) was added 10% Pd/C (0.24 g). The reaction mixture was stirred at 45° C. for 21 hours and then cooled to room temperature. The mixture was filtered through a Celite pad. The organic phase was separated and washed with brine (20 mL). The aqueous phase was extracted with EtOAc (15 mL). The combined organic phases were concentrated in vacuo and the residue was dried in vacuo at 50° C. overnight to give the title compound as a yellow solid (2.5 g, 97.7%).

1. temperaturecooled to room temperature
2. filtrationThe mixture was filtered through a Celite pad
3. customThe organic phase was separated
4. washwashed with brine (20 mL)
5. extractionThe aqueous phase was extracted with EtOAc (15 mL)
6. concentrationThe combined organic phases were concentrated in vacuo
7. customthe residue was dried in vacuo at 50° C. overnight

ORD record

ord-c9929c7fd4d24b6aa7c03dc44f7ed618

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133162B2