Formaldehyde → 6-(3-Bromophenyl)-2-hydroxymethyl-3(2H)-pyridazinone

HRID 649132Notes

Reaction equation

HRID 649132 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:15]=[O:16]>Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:15][OH:16])[N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 128816476-(3-Bromophenyl)pyridazin-3(2H)-one

Product 1

HCID 132358756-(3-Bromophenyl)-2-hydroxymethyl-3(2H)-pyridazinoneYield 40%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

2.51 g of 6-(3-bromophenyl)-3(2H)-pyridazinone, 5 ml of a 37% formalin and 2 drops of concentrated hydrochloric acid were dissolved in 50 ml of methanol, and then the solution was heated under reflux for about 7 hours. The mixture was then left to stand overnight, after which it was filtered and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was extracted with a 1:1 by volume mixture of ethyl acetate and acetone. After distilling the solvent from the extract, there were obtained 1.13 g (yield 40%) of the desired Compound No. 1 in the form of a white solid melting at 228°-229° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for about 7 hours
  3. waitThe mixture was then left
  4. filtrationafter which it was filtered
  5. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  6. extractionThe resulting residue was extracted with a 1:1 by volume mixture of ethyl acetate and acetone
  7. distillationAfter distilling the solvent from the extract

Sources & evidence

ORD record
ord-832344e5442a482ea22d7fa1ec666e71
Source dataset
uspto-grants-1988_04
Patent number
US04738961

Reaction notes

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