4-Nitrophenol → 7-(Benzyloxy)-4-(4-nitrophenoxy)quinoline

HRID 2277382Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)([O-:22])=[O:21].CCN(C(C)C)C(C)C.C(Cl)Cl>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:29][C:26]3[CH:27]=[CH:28][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 115 °C

Procedure

To a suspension of 7-(benzyloxy)-4-chloroquinoline (10 g, 37.1 mmol) and 4-nitrophenol (6.2 g, 44.5 mmol) in toluene (10 mL) was added DIPEA (6.2 g, 48.2 mmol). The reaction mixture was refluxed at 115° C. for 12 hours, then cooled down to room temperature. DCM (50 mL) was added to the mixture, and the resulted solution was washed with 1 M NaOH (30 mL each) several times till the water phase was colorless. The organic phase was concentrated in vacuo to afford a brown solid (13.2 g, 95.7%). The solid was stirred in 95% EtOH (30 mL) at room temperature for 12 hours, and filtered to give the title compound as a gray-brown solid (12.1 g, 91.7%).

Workup

temperaturecooled down to room temperature
washthe resulted solution was washed with 1 M NaOH (30 mL each) several times till the water phase
concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record: ord-ad6b578ce7bb451393ef739e4e7c9944
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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