4-Nitrophenol → HCID 22936514, compound

HRID 2277404Notes

Reaction equation

HRID 2277404 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][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24]([OH:31])[CH:23]=1>C1(C)C(C)=CC=CC=1.C(N(C(C)C)C(C)C)C.CCO>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:31][C:24]3[CH:23]=[CH:22][C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 9804-NitrophenolHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

HCID 22936514HCID 22936514, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 7237O-XyleneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A suspension of 7-(benzyloxy)-4-chloro-6-methoxyquinoline (20.00 g, 70.92 mmol) and p-nitrophenol (13.83 g, 100 mmol) in xylene (40 mL) and N-ethyldiisopropylamine (90 mL) was refluxed for 12 h. The mixture was cooled to rt and diluted with EtOH (200 mL). The solid was collected by filtration and dried in vacuo at 60° C. overnight to give the title compound as a pale yellow solid (22.6 g, 84.3%).

Workup

  1. temperaturewas refluxed for 12 h
  2. filtrationThe solid was collected by filtration
  3. customdried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-c762c143255b4078a680b5ec763b0f7a
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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