Allyl bromide → 6-(4-allyloxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

HRID 1579269Notes

Reaction equation

HRID 1579269 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH2:15](Br)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 1358275406-(4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 214502236-(4-allyloxyphenyl)-4,5-dihydro-3(2H)-pyridazinoneYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A stirred mixture of dry acetone (50 ml), 6-(4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (7 g, 0.037 mole), allyl bromide (3.2 ml, 0.037 mole) and potassium carbonate (5.1 g, 0.037 mole) was heated under reflux for 14 hours. The mixture was diluted with acetone and filtered hot. The inorganic residue was washed with warm acetone and the combined washings and filtrate were evaporated under reduced pressure. The residue was broken up with ether, collected and washed with ether to give 6-(4-allyloxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (6.88 g, 81%, m.p. 130.5°-132°C). Recrystallisation from methanol gave fine white needles of m.p. 134°-135°C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 14 hours
  3. filtrationfiltered hot
  4. washThe inorganic residue was washed with warm acetone
  5. customthe combined washings and filtrate were evaporated under reduced pressure
  6. customcollected
  7. washwashed with ether

Sources & evidence

ORD record
ord-1f3ff69294204f32be7bf536e95fe0f4
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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