Sulfuric Acid → 4,7-Dimethylquinoline

HRID 8221

Reaction equation

HRID 8221 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:14][C:15]([CH:17]=[CH2:18])=O>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5]([C:17]([CH3:18])=[CH:15][CH:14]=[N:8]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6570Methyl vinyl ketoneHCID 7934m-Toluidine

Product 1

HCID 1234994,7-Dimethylquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
12 °C

Procedure

A solution of 3-methyl-phenylamine (1 eq), in 1,4-dioxane is stirred and cooled to approximately 12° C. Sulfuric acid (2 eq.) is slowly added and heated at reflux. Methylvinyl ketone (1.5 eq) is added dropwise into the refluxing solution. The solution is heated for 1 h after addition is complete. The reaction solution is evaporated to dryness and dissolved in methylene chloride. The solution is adjusted to pH 8 with 1 M sodium carbonate and extracted with three times with water. The residue is chromatographed on SiO2 (70/30 hexane/ethylacetate) to yield the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureThe solution is heated for 1 h
  4. additionafter addition
  5. customThe reaction solution is evaporated to dryness
  6. dissolutiondissolved in methylene chloride
  7. extractionextracted with three times with water
  8. customThe residue is chromatographed on SiO2 (70/30 hexane/ethylacetate)

Sources & evidence

ORD record
ord-da6e96936d2f4a35966ec382e248cadc
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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