Sulfuric Acid → HCID 20335516, compound

HRID 1706441Notes

Reaction equation

HRID 1706441 reaction equation
S(=O)(=O)(O)O.[N+]([C:9]1[CH:10]=C(S([O-])(=O)=O)C=[CH:13][CH:14]=1)([O-])=O.[Na+].[CH2:20]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[CH2:21][CH2:22][CH3:23].C(=O)/C=C/C.[OH-].[Na+]>O>[CH2:20]([C:24]1[CH:30]=[C:29]2[C:27](=[CH:26][CH:25]=1)[N:28]=[C:14]([CH3:13])[CH:9]=[CH:10]2)[CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 76944-ButylanilineHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 447466Crotonaldehyde

Product 1

HCID 20335516HCID 20335516, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A stirred mixture of 200 ml. of water, 269 g. of concentrated sulfuric acid and 136 g. of sodium 3-nitrobenzenesulfonate at 75° C. is treated dropwise with 149 g. of 4-butylaniline. The mixture is heated to 105° C. and 117 g. of crotonaldehyde is added dropwise, with stirring, at such a rate that the temperature is maintained at 105° C. The mixture is then heated at 114° C. for 30 minutes, cooled to 80° C. and poured onto chipped ice. The mixture is basified with 50% aqueous sodium hydroxide and steam distilled. The distillate is extracted with dichloromethane. The extract is evaporated at reduced pressure leaving a residue of crude 6-butylquinaldine which is distilled at reduced pressure; b.p. 104°-106° C./0.5 mm. This product is further purified by dissolving it in 600 ml. of ether and treating the solution with 23 ml. of acetic anhydride. After standing for 20 minutes, the solution is extracted with 500 ml. of 10% hydrochloric acid. The acid extract is basified with 50% aqueous sodium hydroxide and extracted with ether. The ether extract is washed with water, dried and evaporated to give a residue of purified 6-butylquinaldine.

Workup

  1. additionA stirred mixture of 200 ml
  2. temperatureat such a rate that the temperature is maintained at 105° C
  3. temperatureThe mixture is then heated at 114° C. for 30 minutes
  4. temperaturecooled to 80° C.
  5. additionpoured
  6. distillationdistilled
  7. extractionThe distillate is extracted with dichloromethane
  8. customThe extract is evaporated at reduced pressure
  9. customleaving a residue of crude 6-butylquinaldine which
  10. distillationis distilled at reduced pressure
  11. customThis product is further purified
  12. dissolutionby dissolving it in 600 ml
  13. additionof ether and treating the solution with 23 ml
  14. extractionthe solution is extracted with 500 ml
  15. extractionThe acid extract
  16. extractionextracted with ether
  17. extractionThe ether extract
  18. washis washed with water
  19. customdried
  20. customevaporated

Sources & evidence

ORD record
ord-61148a88fae847ba8438d192fe3e642c
Source dataset
uspto-grants-1980_06
Patent number
US04207320

Reaction notes

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