Sulfuric Acid → 6-Bromo-4-methylquinoline

HRID 915527Notes

Reaction equation

HRID 915527 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:14][C:15]([CH:17]=[CH2:18])=O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:8]=[CH:14][CH:15]=[C:17]2[CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6570Methyl vinyl ketoneHCID 78074-Bromoaniline

Product 1

HCID 124753626-Bromo-4-methylquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Stir a solution of 4-bromo-phenylamine (1 eq), in 1,4-dioxane and cool to approximately 12° C. Slowly-add sulfuric acid (2 eq) and heat at reflux. Add methylvinyl ketone (1.5 eq) dropwise into the refluxing solution. Heat the solution for 1 hour after addition is complete. Evaporate the reaction solution to dryness and dissolve in methylene chloride. Adjust the solution to pH 8 with 1 M sodium carbonate and extract three times with water. Chromatograph the residue on SiO2 (70/30 hexane/ethyl acetate) to obtain the desired subtitled intermediate. MS ES+ m/e =158.2 (M+1).

Workup

  1. temperatureat reflux
  2. temperatureHeat the solution for 1 hour
  3. additionafter addition
  4. customEvaporate the reaction solution to dryness
  5. dissolutiondissolve in methylene chloride
  6. extractionextract three times with water

Sources & evidence

ORD record
ord-0701f81994a24c0ea3c85b17128cb255
Source dataset
uspto-grants-2007_09
Patent number
US07265225B2

Reaction notes

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