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

HRID 596674ノート

反応式

HRID 596674 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-64961a1066dd40faad930610a01e088c
出典データセット
uspto-grants-1977_03
特許番号
US04011321

反応ノート

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