Hydrazine hydrate (1:1) → HCID 21450278, compound

HRID 1579267Notes

Reaction equation

HRID 1579267 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH2:13][CH2:14][C:15](OC)=[O:16])=O)=[CH:9][C:8]=1[OH:21])[CH:5]=[CH2:6]>C(O)(=O)C>[CH2:4]([C:7]1[CH:20]=[CH:19][C:10]([C:11]2[CH2:13][CH2:14][C:15](=[O:16])[NH:2][N:3]=2)=[CH:9][C:8]=1[OH:21])[CH:5]=[CH2:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21450289HCID 21450289, compound

Product 1

HCID 21450278HCID 21450278, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydrazine hydrate (4.5 ml, 0.09 mole) was added to a stirred solution of methyl 3-(4-allyl-3-hydroxybenzoyl)propionate (5.6 g, 0.023 mole) in glacial acetic acid (60 ml) and the mixture heated under reflux for one hour. Evaporation under reduced pressure gave a residue which was triturated with water to give 6-(4-allyl-3-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (5 g, m.p. 175°-178°C, 96%). The pure pyridazinone, recrystallised from ethanol had m.p. 178°-180°C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for one hour
  3. customEvaporation under reduced pressure
  4. customgave a residue which
  5. customwas triturated with water

Sources & evidence

ORD record
ord-345befcbfee74a5b98cf35755c7603b9
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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