Acetaldehyde → HCID 19788471, compound

HRID 1292709Notes

Reaction equation

HRID 1292709 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH:12](=O)[CH3:13].CC1C=CC(S)=CC=1>C(O)C>[CH2:12]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)[CH3:13]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 78114-MethylbenzenethiolHCID 119115-Aminoquinoline

Product 1

HCID 19788471HCID 19788471, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-aminoquinoline (7.2 g, 0.05 mol), acetaldehyde (2.6 g, 0.06 mol) and 4-thiocresol (6.8 g, 0.055 mol) in ethanol (100 ml) was stirred at reflux for 4 h. The reaction mixture was evaporated under reduced pressure and the residue dissolved in ethanol (100 ml). Sodium borohydride (10 g) was then added to the reaction mixture in portions maintaining the temperature below 5° C. This reaction mixture was stirred at reflux for 2 h and cooled to room temperature. Water (40 ml) was then added and the mixture was stirred for a further 25 min at reflux. The pH of the mixture was then adjusted to pH8 with 2N NaOH and the product was extracted with dichloromethane (4×100 ml). The dichloromethane extracts were combined and washed with water (250 ml) before being dried over MgSO4. The solvent was then removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexane. The solvent in the eluent was evaporated to give 5.4 g of a yellow solid which was used without further purification.

Workup

  1. temperatureat reflux for 4 h
  2. customThe reaction mixture was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in ethanol (100 ml)
  4. additionSodium borohydride (10 g) was then added to the reaction mixture in portions
  5. temperaturemaintaining the temperature below 5° C
  6. stirringThis reaction mixture was stirred
  7. temperatureat reflux for 2 h
  8. additionWater (40 ml) was then added
  9. stirringthe mixture was stirred for a further 25 min
  10. temperatureat reflux
  11. extractionthe product was extracted with dichloromethane (4×100 ml)
  12. washwashed with water (250 ml)
  13. dry with materialbefore being dried over MgSO4
  14. customThe solvent was then removed under reduced pressure
  15. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate in hexane
  16. customThe solvent in the eluent was evaporated

Sources & evidence

ORD record
ord-c372c28b576d4985b19070cbe4df72b0
Source dataset
uspto-grants-2007_07
Patent number
US07238228B2

Reaction notes

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