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

HRID 596674노트

반응식

HRID 596674 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-64961a1066dd40faad930610a01e088c
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04011321

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