Glycerol → 5-Bromo-8-methylquinoline

HRID 1027597

Reaction equation

HRID 1027597 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].O[CH2:11][CH:12]([CH2:14]O)O.[N+](C1C=CC=CC=1)([O-])=O.[OH-].[Na+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]2[C:8]=1[CH:11]=[CH:12][CH:14]=[N:7]2

Participants

7

Reactant 4

HCID 753GlycerolHCID 7416NitrobenzeneHCID 14798Sodium HydroxideHCID 27348055-Bromo-o-toluidine

Product 1

HCID 47150225-Bromo-8-methylquinolineYield 67.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-Bromo-2-methylaniline (7.44 g), glycerol (7.4 g), nitrobenzene (4.9 g) in 75% sulfuric acid (20 ml) was heated at 150° C. for 3 hrs. The solution was cooled to 0° C. then carefully neutralized with aqueous sodium hydroxide. The reaction mixture became a dark gum and was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with saturated brine, then dried with sodium sulphate and the solvent removed in vacuo. The crude product was purified by column chromatography (dichloromethane) to afford the title compound as a solid (6 g). 1H-NMR (CDCl3, 400 MHz) 8.91 (m, 1H), 8.51 (m, 1H), 7.7 (m, 1H), 7.50 (m, 1H), 7.4 (m, 1H), 2.72 (s, 3H).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried with sodium sulphate
  4. customthe solvent removed in vacuo
  5. customThe crude product was purified by column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-e8c82a859e60407184863d6af6fb5253
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Linked notes

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