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

HRID 2277387Notes

Reaction equation

[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].Br[CH2:25][CH2:26][OH:27]>CN(C=O)C>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:25][CH2:26][OH:27])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 4-(4-nitrophenoxy)quinolin-7-ol (2.82 g, 10 mmol) in DMF (20 mL) was added KOH pellets (1.12 g, 20 mmol) and 2-bromoethanol (1.87 g, 15 mmol) at room temperature. The reaction was then warmed up to 45° C. and stirred for 12 hours. The mixture was then concentrated in vacuo and the residue was purified by a column chromatography on silica gel (EtOAc/PE=1:1) to give the title compound as a pale yellow solid (417 mg, 12.8%).

Workup

concentrationThe mixture was then concentrated in vacuo
customthe residue was purified by a column chromatography on silica gel (EtOAc/PE=1:1)

Sources & evidence

ORD record: ord-490cdf0df1d54f318a09df8d2195db5f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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