Formaldehyde → HCID 86613909, compound

HRID 503972Notes

Reaction equation

HRID 503972 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]([CH3:13])[C:10](=[O:14])[CH:9]=[CH:8]2.[CH2:15]=[O:16].S(=O)(=O)(O)O.C1N2CN3CN(C2)CN1C3>Cl.ClCCl>[CH3:1][O:2][C:3]1[C:12]2[N:11]([CH3:13])[C:10](=[O:14])[CH:9]=[CH:8][C:7]=2[C:6]([CH:15]=[O:16])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 7427918-METHOXY-1-METHYL-1H-QUINOLIN-2-ONE

Product 1

HCID 86613909HCID 86613909, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

8-Methoxy-1-methyl-1H-quinolin-2-one (21.14 g, 0.11 mol) and paraformaldehyde (10.6 g) were suspended in concentrated hydrochloric acid (105 ml), and 4 ml of concentrated sulfuric acid was added, followed by stirring at 70 to 80° C. for 2.5 hours. After cooling to room temperature, ice water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was dissolved in 400 ml of chloroform, and hexamethylenetetramine (4.25 g, 0.03 mol) was added, followed by heating under reflux for 2.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. 50% acetic acid (110 ml) was added to the residue, and stirring was carried out at 100° C. for 2 hours. After cooling to room temperature, water was added, and the insoluble matter was collected by filtration and dried to thereby obtain 13.81 g (yield: 57%) of 8-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-5-carboxaldehyde as a light yellow powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in 400 ml of chloroform
  6. temperatureby heating
  7. temperatureunder reflux for 2.5 hours
  8. temperatureAfter cooling to room temperature
  9. distillationthe solvent was distilled off under reduced pressure
  10. addition50% acetic acid (110 ml) was added to the residue
  11. stirringstirring
  12. waitwas carried out at 100° C. for 2 hours
  13. temperatureAfter cooling to room temperature
  14. additionwater was added
  15. filtrationthe insoluble matter was collected by filtration
  16. customdried

Sources & evidence

ORD record
ord-0b57cb2361ce4a46ae9cb0ddf0d16b50
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

Loading…