Anisole → 4-(3-Hydroxypropyl)-1,2-dihydro-3,6-pyridazinedione

HRID 2233201Notes

Reaction equation

HRID 2233201 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9](CC2C=CC(OC)=CC=2)[NH:8][C:7](=[O:21])[CH:6]=1.C1(OC)C=CC=CC=1>C(O)(C(F)(F)F)=O>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:10](=[O:11])[NH:9][NH:8][C:7](=[O:21])[CH:6]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 675265645-(3-Hydroxypropyl)-1-{[4-(methyloxy)phenyl]methyl}-1,2-dihydro-3,6-pyridazinedione

Product 1

HCID 675266004-(3-Hydroxypropyl)-1,2-dihydro-3,6-pyridazinedioneYield 92.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

5-(3-Hydroxypropyl)-1-{[4-(methyloxy)phenyl]methyl}-1,2-dihydro-3,6-pyridazinedione (2.734 g) was treated with anisole (10 ml) and TFA (100 ml) and stirred at 40° C. overnight. The solution was cooled, evaporated to dryness and kept under high vacuum for 30 minutes. The residue was taken up in methanol (150 ml), refluxed for 12 hours, cooled and evaporated. The residue was kept for 1 hour under high vacuum, triturated under ether and the solid was filtered off. Drying under vacuum gave the product as a solid (1.48 g, 92%).

Workup

  1. temperatureThe solution was cooled
  2. customevaporated to dryness
  3. waitkept under high vacuum for 30 minutes
  4. temperaturerefluxed for 12 hours
  5. temperaturecooled
  6. customevaporated
  7. waitThe residue was kept for 1 hour under high vacuum
  8. customtriturated under ether
  9. filtrationthe solid was filtered off
  10. customDrying under vacuum

Sources & evidence

ORD record
ord-adb0a188ae304ba483867c6e82b83733
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

Loading…