Acetic Acid → 6-[2-(2-hydroxy-3-isopropyl-aminopropoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 596674Notes

Reaction equation

HRID 596674 reaction equation
[OH2:1].[NH2:2][NH2:3].O[CH:5]([CH2:22][NH:23]C(C)C)[CH2:6][O:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]([CH2:12][CH2:13][C:14]([O:16]C)=O)=O.[C:27](=O)([O-])[O-].[Na+].[Na+].[C:33](O)(=O)[CH3:34]>O>[OH:1][CH:5]([CH:22]([NH2:23])[CH:33]([CH3:34])[CH3:27])[CH2:6][O:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]1[CH2:12][CH2:13][C:14](=[O:16])[NH:2][N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 20309568Methyl 3-[2-(2-hydroxy-3-isopropylaminopropoxy)benzoyl]propionate

Product 1

HCID 706375736-[2-(2-hydroxy-3-isopropyl-aminopropoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydrazine hydrate (4.65 ml, 0.09 mole) was added to a solution of methyl 3-[2-(2-hydroxy-3-isopropylaminopropoxy) benzoyl]propionate (10 g, 0.03 mole) in glacial acetic acid (80 ml) and the solution was heated under reflux for one hour. Evaporation under reduced pressure gave an oil (25.5 g.) which was dissolved in water, treated with an excess of sodium carbonate solution and extracted with dichloromethane. Evaporation of the dried extracts gave an oil (10.3 g.) which was purified on a silica column by elution with a mixture of chloroform and methanol to give 6-[2-(2-hydroxy-3-isopropyl-aminopropoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone (6.25 g, 66%), m.p. 124°-126° C. The hydrochloride, crystallised from 2-propanol, had m.p. 162°-164.5° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for one hour
  3. customEvaporation under reduced pressure
  4. customgave an oil (25.5 g.) which
  5. extractionextracted with dichloromethane
  6. customEvaporation of the dried extracts
  7. customgave an oil (10.3 g.) which
  8. customwas purified on a silica column by elution with a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-64961a1066dd40faad930610a01e088c
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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