4-Nitrophenol → 5,7-Dimethoxy-4-(4-nitrophenoxy)quinoline

HRID 573415Notes

Reaction equation

HRID 573415 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[CH:9][C:10]=2[O:12][CH3:13])[N:5]=[CH:4][CH:3]=1.[CH:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([OH:25])[CH:17]=1>ClC1C=CC=CC=1>[CH3:13][O:12][C:10]1[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=[C:6]2[C:11]=1[C:2]([O:25][C:18]1[CH:17]=[CH:16][C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=1)=[CH:3][CH:4]=[N:5]2

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 178804724-Chloro-5,7-dimethoxyquinoline

Product 1

HCID 895814265,7-Dimethoxy-4-(4-nitrophenoxy)quinoline

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

4-Chloro-5,7-dimethoxyquinoline (100 mg, 0.40 mmol) and p-nitrophenol (124 mg, 0.89 mmol) in chlorobenzene (2 mL) was heated at reflux for 14 h. Then the reaction mixture was cooled to rt, filtered, and the residue washed with toluene. The solid was suspended in 10% NaOH solution and stirred for 1 h at rt. The yellow solid was collected and washed with EtOAc to give 5,7-dimethoxy-4-(4-nitrophenoxy)quinoline. LCMS m/z=327 (M+1); 1H NMR (CDCl3) δ: 8.60 (d, 1H, J=6.0 Hz), 8.44 (d, 2, J=8.8 Hz), 7.72 (s, 1H), 7.35 (d, 2H, J=8.4 Hz) 6.71 (s, 1H), 6.69 (d, 2H, J=6.4 Hz), 4.08 (s, 3H), 3.97 (s, 3H).

Workup

  1. temperatureat reflux for 14 h
  2. filtrationfiltered
  3. washthe residue washed with toluene
  4. customThe yellow solid was collected
  5. washwashed with EtOAc

Sources & evidence

ORD record
ord-64975191131d4ccf935572dc23372c44
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

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