Propanal → HCID 28445232, compound

HRID 1418028Notes

Reaction equation

HRID 1418028 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)[CH2:13][CH3:14]>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)[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 527PropanalHCID 119115-Aminoquinoline

Product 1

HCID 28445232HCID 28445232, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g of 5-aminoquinoline, 3 ml of propionaldehyde and 4.7 g of para-thiocresol are dissolved in 100 ml of ethanol in a 250 ml round-bottomed flask. The reaction mixture is heated at reflux for 2 hours and then evaporated to dryness. The residue is dissolved in 100 ml of ethanol and cooled in an ice bath and then 6.5 g of sodium borohydride are added portionwise. When addition is complete, the reaction mixture is heated at reflux for 2 hours and then, successively, 30 ml of water are added, the mixture is basified with 20 ml of concentrated sodium hydroxide and stirred for 15 minutes and the organic solvents are evaporated. Extraction is carried out with dichloromethane and the organic phase is washed with water and then dried over sodium sulphate. The organic phase is evaporated to dryness and the residue is purified on a column of silica gel, eluent: ethyl acetate, to obtain 4 g of an oil which crystallizes. 1H NMR (CDCl3): 1.05 (t, J=3H, --CH3), 1.82-1.71 (m, 2H, --CH2 --CH3), 3.15-3.26 (m, 2H, --NH--CH2 --), 4.37 (sl, 1H, --NH--), 6.61 (dd, J=1.0, J=8.6, 1H, H4), 7.26 (dd, J=4.2, J=8.6, 1H, H6), 7.44-7.59 (m, 2H, H3, H2), 8.12 (dd, J=0.95, J=8.6, 1H, H8), 8.84 (dd, J=1.5, J=4.2, H2).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. customevaporated to dryness
  4. dissolutionThe residue is dissolved in 100 ml of ethanol
  5. temperaturecooled in an ice bath
  6. addition6.5 g of sodium borohydride are added portionwise
  7. additionWhen addition
  8. temperaturethe reaction mixture is heated
  9. temperatureat reflux for 2 hours
  10. additionsuccessively, 30 ml of water are added
  11. customthe organic solvents are evaporated
  12. extractionExtraction
  13. washthe organic phase is washed with water
  14. dry with materialdried over sodium sulphate
  15. customThe organic phase is evaporated to dryness
  16. customthe residue is purified on a column of silica gel, eluent

Sources & evidence

ORD record
ord-ba8c3d9c4c034eb4af6e149a93da6f09
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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