3-Fluoro-4-nitrophenol → 6-Cyano-4-(3-fluoro-4-nitrophenoxy)-7-(2-methoxyethoxy)quinoline

HRID 1433344Notes

Reaction equation

HRID 1433344 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:19][C:20]1[CH:21]=[C:22]([OH:29])[CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27]>ClC1C=CC=CC=1>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])[N:5]=[CH:4][CH:3]=[C:2]2[O:29][C:22]1[CH:23]=[CH:24][C:25]([N+:26]([O-:28])=[O:27])=[C:20]([F:19])[CH:21]=1)#[N:13]

Participants

4

Reactant 2

HCID 5209483-Fluoro-4-nitrophenolHCID 226465224-Chloro-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 229365736-Cyano-4-(3-fluoro-4-nitrophenoxy)-7-(2-methoxyethoxy)quinolineYield 62.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

4-Chloro-6-cyano-7-(2-methoxyethoxy)quinoline (1.7 g) and 3-fluoro-4-nitrophenol (2.0 g) were suspended in chlorobenzene (20 ml), and the suspension was heated to reflux for 6 hours. After completion of the reaction, the solvent was distilled off, ethyl acetate was added, and a solid precipitated. The solid was filtered out and washed with ether, washed with 1N sodium hydroxide water and with water, and then dried to obtain 1.55 g of the title compound.

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 6 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. additionethyl acetate was added
  6. customa solid precipitated
  7. filtrationThe solid was filtered out
  8. washwashed with ether
  9. washwashed with 1N sodium hydroxide water and with water
  10. customdried

Sources & evidence

ORD record
ord-a5d23096790d411896c9bf53441d7f88
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

Loading…