Glycerol → 2-(1-(7-Fluoroquinolin-6-yl)ethyl)isoindoline-1,3-dione

HRID 456052Notes

Reaction equation

HRID 456052 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12](O)[CH3:13].[N+:15]([C:18]1C=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-])=O.S(=O)(=O)(O)[OH:25].O[CH2:30][CH:31]([CH2:33][OH:34])O>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([N:15]1[C:18](=[O:25])[C:19]2[C:31](=[CH:30][CH:22]=[CH:21][CH:20]=2)[C:33]1=[O:34])[CH3:13]

Participants

5

Reactant 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 669272001-(7-Fluoroquinolin-6-yl)ethanol

Product 1

HCID 669272652-(1-(7-Fluoroquinolin-6-yl)ethyl)isoindoline-1,3-dioneYield 49.8%

Procedure

A mixture of 4-bromo-3,5-difluoro-phenylamine (i) (6.0 g, 28.8 mmole), 1.82 g ferrous sulfate, 8.6 mL glycerol, 1.79 mL nitrobenzene, and 5.0 mL concentrated sulfuric acid was heated gently. After the first vigorous reaction, the mixture was boiled for five hours. Nitrobenzene was removed by distillation in vacuo. The aqueous solution was acidified with glacial acetic acid, and dark brown precipitate separated, which was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1) to give 6-bromo-5,7-difluoroquinoline (ii) as a white solid (3.5 g, 49.8%).

Workup

  1. temperaturewas heated gently
  2. customAfter the first vigorous reaction
  3. customNitrobenzene was removed by distillation in vacuo
  4. customseparated
  5. customwhich was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1)

Sources & evidence

ORD record
ord-5f1fe484b15a4357813973093ab20fe1
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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