3,4-Dinitrophenol → 4-(3,4-Dinitro-phenoxy)-quinoline

HRID 491654Notes

Reaction equation

HRID 491654 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:16]=[C:17]([OH:24])[CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])([O-:14])=[O:13]>C(Cl)Cl.[OH-].[Na+]>[N+:12]([C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[O:24][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 113483,4-DinitrophenolHCID 691404-Chloroquinoline

Product 1

HCID 177560764-(3,4-Dinitro-phenoxy)-quinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Chloroquinoline (4.3 g, 26.3 mmol) and 3,4-dinitrophenol (41.5 g, 24.4 mmol) were heated at 150° C. for 30 min. The mixture was cooled to RT and the residue was dissolved in CH2Cl2. The mixture was diluted in NaOH 2 M and extracted with CH2Cl2. The organic phase was dried, filtered and evaporated. The residue was diluted in EtOAc and filtered through a silica pad. The solvent was removed to give the title compound as a brown solid.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. additionThe residue was diluted in EtOAc
  6. filtrationfiltered through a silica pad
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-2e6b9db57ddb4976b59563a59f01828d
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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