4-Nitrophenol → 6-Cyano-7-(2-methoxyethoxy)-4-(4-nitrophenoxy)quinoline

HRID 1433342

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)([O-:21])=[O:20].N1C(C)=CC=CC=1C>C(OCC)(=O)C>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])[N:5]=[CH:4][CH:3]=[C:2]2[O:28][C:25]1[CH:26]=[CH:27][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=1)#[N:13]

Participants

Conditions

Temperature: 155 °C

Procedure

A mixture of 4-chloro-6-cyano-7-(2-methoxyethoxy)quinoline (3 g), 4-nitrophenol (3.17 g) and 2,6-lutidine (2.7 ml) was heated and stirred in an oil bath at 155° C. for 1.5 hours. After completion of the reaction, ethyl acetate was added, and the precipitated solid was filtered out. The solid was washed with 1N sodium hydroxide water and then with water and dried to obtain 1.8 g of the title compound.

Workup

temperaturewas heated
additionwas added
filtrationthe precipitated solid was filtered out
washThe solid was washed with 1N sodium hydroxide water
dry with materialwith water and dried

Sources & evidence

ORD record: ord-05cf31fa4a5e4d76aac9fd704d970649
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612092B2

Linked notes

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