3,4-Dinitrophenol → 4-(3,4-Dinitrophenoxy)-6,7-dimethoxyquinoline

HRID 491669Notes

Reaction equation

HRID 491669 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2Cl.[N+:16]([C:19]1[CH:20]=[C:21]([OH:28])[CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])([O-:18])=[O:17]>CO>[N+:16]([C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])[O:28][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 113483,4-DinitrophenolHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 177563934-(3,4-Dinitrophenoxy)-6,7-dimethoxyquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6,7-dimethoxy-4-chloroquinoline (0.35 g, 1.6 mmol) and 3,4-dinitrophenol (0.85 g, 4.6 mmol) was heated to 150° C. for 4 h. The mixture was cooled at RT and MeOH added. The reaction was stirred for 3 h. The precipitate filtered out and was washed with MeOH to afford 4-(3,4-dinitrophenoxy)-6,7-dimethoxyquinoline.

Workup

  1. temperatureThe mixture was cooled at RT
  2. filtrationThe precipitate filtered out
  3. washwas washed with MeOH

Sources & evidence

ORD record
ord-97f2b4e341514bf8995ed2ea4747d2ad
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

Loading…