2-((4-(4-Nitrophenoxy)quinolin-7-yl)oxy)ethanol → 2-((4-(4-Aminophenoxy)quinolin-7-yl)oxy)ethanol

HRID 2277388Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

To a suspension of 2-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)ethanol (0.32 g, 1 mmol), HCOOK (0.59 g, 7 mmol) in water (1 mL) and THF (3 mL) was added 10% Pd/C (0.03 g). The reaction was stirred at 45° C. for 4 hours. The mixture was diluted with EtOAc (5 mL), filtered through a Celite pad. The filtrate was concentrated in vacuo, washed with a mixture of 95% ethanol (1 mL) and water (5 mL). The solid was collected by filtration and dried in vacuo at 50° C. overnight to give the title compound as a pale yellow solid (140 mg, 47.3%).

Workup

filtrationfiltered through a Celite pad
concentrationThe filtrate was concentrated in vacuo
washwashed with a mixture of 95% ethanol (1 mL) and water (5 mL)
filtrationThe solid was collected by filtration
customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record: ord-2e4d2c0706af4dc7b1e03fec1aae307f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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