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

HRID 656952Notes

Reaction equation

HRID 656952 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 MeOH (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-5429978f46074949b7efe0b3222da6a0
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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