Sulfuric Acid → 6-Bromo-8-methylquinoline

HRID 655234Notes

Reaction equation

HRID 655234 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[N+]([C:13]1[CH:18]=CC=C[CH:14]=1)([O-])=O.S(=O)(=O)(O)O>OCC(CO)O>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[C:4]([CH3:9])[CH:3]=1)[N:6]=[CH:18][CH:13]=[CH:14]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 114234-Bromo-2-methylaniline

Product 1

HCID 224034106-Bromo-8-methylquinoline

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

A mixture of 10 g of 4-bromo-2-methylaniline, 3.3 g of ferrous sulfate, 20.4 g of glycerol, 4.06 g of nitrobenzene and 11.5 ml of concentrated sulfuric acid was heated gently. After the first vigorous reaction, the mixture was boiled for 3 h under reflux and then evaporated to remove t nitrobenzene. The solution was added std. aq.NaHCO3 and extracted with dichloromethane, dried with Na2SO4 and concentrated to give solid. The solid was purified with flash column chromatography to return the title compound (9.5 g, 80%). 1H NMR (CDCl3, 300 MHz) δ 8.92 (m, 1H), 8.01 (m, 1H), 7.81 (d, 1H), 7.66 (m, 1H), 7.43 (m, 1H), 2.79 (s, 3H).

Workup

  1. temperaturewas heated gently
  2. customAfter the first vigorous reaction
  3. temperatureunder reflux
  4. customevaporated
  5. customto remove t nitrobenzene
  6. additionThe solution was added std
  7. extractionNaHCO3 and extracted with dichloromethane
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated
  10. customto give solid
  11. customThe solid was purified with flash column chromatography

Sources & evidence

ORD record
ord-227e052f4b254e398841384dca6709fb
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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