Glycerol → 8-Bromo-6-(propan-2-yl)quinoline

HRID 2063578Notes

Reaction equation

HRID 2063578 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:11].[CH2:12](O)[CH:13](O)[CH2:14]O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[OH-].[Na+]>CS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[CH:5]=[C:4]2[C:3]=1[N:11]=[CH:14][CH:13]=[CH:12]2

Participants

6

Reactant 4

HCID 753GlycerolHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 5213372-Bromo-4-isopropylaniline

Product 1

HCID 218655558-Bromo-6-(propan-2-yl)quinolineYield 65%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-bromo-4-isopropyl-phenylamine (1.72 g, 8.0 mmol), propane-1,2,3-triol (1.84 g, 2.5 equiv), FeSO4 (0.067 g, 0.30 equiv), 3-nitrobenzenesulfonic acid sodium salt (1.13 g, 0.63 equiv) in 4.5 mL of methanesulfonic acid was heated to 135° C. for 3 hours and then cooled down to room temperature. 2 N Aqueous NaOH (˜40 mL) was added and the mixture was extracted with EtOAc (3×50 mL). The organic layer was washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography using 5% to 20% EtOAc in hexane to afford the title compound (1.3 g, 65%) as dark brown solid. MS (ES) m/z 250.2 (M+H+).

Workup

  1. temperaturecooled down to room temperature
  2. extractionthe mixture was extracted with EtOAc (3×50 mL)
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9c76353c5fd64fe1b064e41ed2538e0e
Source dataset
uspto-grants-2012_10
Patent number
US08288373B2

Reaction notes

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