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

HRID 2277385Notes

Reaction equation

[CH3:1][C:2]([OH:26])([CH3:25])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1.C(O[K])=O>O.C1COCC1.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:9]2[C:8]3[C:13](=[CH:14][C:5]([O:4][CH2:3][C:2]([CH3:25])([OH:26])[CH3:1])=[CH:6][CH:7]=3)[N:12]=[CH:11][CH:10]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 45 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-c9929c7fd4d24b6aa7c03dc44f7ed618
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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