Cyclopropyl methyl ketone → 1-Cyclopropyl-3-(3-pyridazinyl)-1,3-propanedione

HRID 1076689Notes

Reaction equation

HRID 1076689 reaction equation
C(O[C:4]([C:6]1[N:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])C.[CH:12]1([C:15]([CH3:17])=[O:16])[CH2:14][CH2:13]1.C[O-].[Na+]>C1C=CC=CC=1>[CH:12]1([C:15](=[O:16])[CH2:17][C:4]([C:6]2[N:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[O:5])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 10942334Sodium MethoxideHCID 14452007Ethyl pyridazine-3-carboxylate

Product 1

HCID 123605611-Cyclopropyl-3-(3-pyridazinyl)-1,3-propanedione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 4.0 g. of ethyl-3-pyridazinecarboxylate, 4.4 g. of cyclopropylmethyl ketone and 1.6 g. of sodium methoxide in 100 ml. of benzene is heated under reflux for 5 hours. The mixture is diluted with 300 ml. of water and the benzene phase is separated. The aqueous mixture is made weakly acidic with dilute hydrochloric acid and extracted with chloroform. The chloroform solution is dried over magnesium sulfate and concentrated under reduced pressure to yield straw-colored crystals which are recrystallized from acetonitrile to give cream-colored crystals, melting point 85°-87°C.

Workup

  1. additionA stirred mixture of 4.0 g
  2. temperatureunder reflux for 5 hours
  3. additionThe mixture is diluted with 300 ml
  4. customof water and the benzene phase is separated
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform solution is dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto yield straw-colored crystals which
  9. customare recrystallized from acetonitrile
  10. customto give cream-colored crystals, melting point 85°-87°C.

Sources & evidence

ORD record
ord-dee5d170abcf4ec79a490c1160d16b96
Source dataset
uspto-grants-1976_05
Patent number
US03957805

Reaction notes

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