Chlorobenzene → 7-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline

HRID 1754245Notes

Reaction equation

HRID 1754245 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.[F:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:24]=1[OH:32].ClC1C=CC=CC=1>C(=O)([O-])[O-].[Na+].[Na+]>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:32][C:24]3[CH:25]=[CH:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:23]=3[F:22])=[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

5

Reactant 3

HCID 7964ChlorobenzeneHCID 98252-Fluoro-4-nitrophenolHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

HCID 229354107-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinolineYield 39%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 7-benzyloxy-4-chloro-6-methoxy-quinoline (2.04 g, 6.8 mmol), 2-fluoro-4-nitrophenol (2.34 g 14.9 mmol) and chlorobenzene (40 ml) was stirred at reflux temperature for 2 days. The reaction mixture was cooled, diluted with saturated sodium carbonate solution (30 ml) and stirred for 3 hours. The precipitate was filtered and the filtrate was separated. The aqueous layer was extracted with chloroform (3×30 ml). The organic layers were combined, washed with water and dried over sodium sulfate. The solvent was removed by evaporation under the reduced pressure. The residue was purified by column chromatography. The pure product was solidified under diisopropyl ether to give 1.11 g of product [F]. Yield: 39%.

Workup

  1. temperatureat reflux temperature for 2 days
  2. temperatureThe reaction mixture was cooled
  3. stirringstirred for 3 hours
  4. filtrationThe precipitate was filtered
  5. customthe filtrate was separated
  6. extractionThe aqueous layer was extracted with chloroform (3×30 ml)
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed by evaporation under the reduced pressure
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f1779da560174b9792c546f1d6bb0a49
Source dataset
uspto-grants-2015_10
Patent number
US09169241B2

Reaction notes

Loading…