Sulfuric Acid → 6-Butylquinoline

HRID 1816190Notes

Reaction equation

HRID 1816190 reaction equation
[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[N+]([C:15]1[CH:16]=C(S(O)(=O)=O)C=C[CH:20]=1)([O-])=O.B(O)(O)O.S(=O)(=O)(O)O.[OH-].[Na+]>OCC(CO)O>[CH2:1]([C:5]1[CH:11]=[C:10]2[C:8](=[CH:7][CH:6]=1)[N:9]=[CH:16][CH:15]=[CH:20]2)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 73873-Nitrobenzenesulfonic acidHCID 7628Boric AcidHCID 76944-ButylanilineHCID 14798Sodium Hydroxide

Product 1

HCID 820926-ButylquinolineYield 66.6%

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Conditions

Temperature
140 °C

Procedure

38.6 (259 mM) of 4-butylaniline, 80.5 g (875 mM) of glycerin, 25.0 g of m-nitrobenzenesulfonic acid, 7.6 g of ferric sulfate and 13.2 g of boric acid were placed in a 500 ml-three necked flask. To the mixture, 47.4 ml of conc. sulfuric acid was added dropwise over 20 minutes with stirring on an ice bath, whereby the temperature was increased from 8° C. to 50° C. The mixture was heat-refluxed at 135-145° C. for 2 hours under stirring. After the reaction, the reaction mixture was poured into ice water and alkalinized with 20% NaOH aqueous solution to pH=11, followed by extraction with toluene. The organic layer was washed with water and evaporated. The residue was purified by silica gel column chromatography (eluent: toluene/THF) to obtain 31.9 g of 6-butylquinoline (yield: 66.6%).

Workup

  1. temperaturewhereby the temperature was increased from 8° C. to 50° C
  2. stirringunder stirring
  3. customAfter the reaction
  4. extractionfollowed by extraction with toluene
  5. washThe organic layer was washed with water
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (eluent: toluene/THF)

Sources & evidence

ORD record
ord-37cde85e0a9847f18413448029d17c40
Source dataset
uspto-grants-2005_04
Patent number
US06884477B1

Reaction notes

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