Formaldehyde → 3(2H)-Pyridazinone, 6-(4-chlorophenoxy)-2-(hydroxymethyl)-

HRID 1448944Notes

Reaction equation

HRID 1448944 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.[CH2:16]=[O:17]>C(O)C>[OH:17][CH2:16][N:11]1[C:10](=[O:13])[CH:9]=[CH:8][C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=2)=[N:12]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 20351305HCID 20351305, compound

Product 1

HCID 30525783(2H)-Pyridazinone, 6-(4-chlorophenoxy)-2-(hydroxymethyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a solution, at reflux, of 7 g 6-(4-chlorophenoxy)-3-pyridazinone in 100 ml ethanol, there are poured 30 ml of a 20% aqueous formaldehyde solution, and then after 1 hour a further 30 ml. After refluxing for 3 hours, the solution is concentrated to half, and 100 ml water are introduced into the mixture from which 4.5 g of final product are extracted in chloroform. After recrystallisation from benzene, the product melts at 162° C. (with decomposition)

Workup

  1. temperatureAfter refluxing for 3 hours
  2. concentrationthe solution is concentrated to half, and 100 ml water
  3. additionare introduced into the mixture from which 4.5 g of final product
  4. extractionare extracted in chloroform
  5. customAfter recrystallisation from benzene

Sources & evidence

ORD record
ord-01ecc60a2bc3496295df0edea031bf1f
Source dataset
uspto-grants-1980_02
Patent number
US04188388

Reaction notes

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