Ammonia → 6-Isopropyl-3-pyridazinone

HRID 1042003노트

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HRID 1042003 반응식
O.[C:2]([OH:6])(=O)[CH:3]=[O:4].[CH3:7][C:8]([CH:10]([CH3:12])[CH3:11])=O.[NH3:13].[OH-].[NH3+:15]N>O>[OH:6][CH:2]1[C:10]([CH3:12])([CH3:11])[C:8]([CH3:7])=[N:15][NH:13][C:3]1=[O:4].[CH:10]([C:8]1[CH:7]=[CH:3][C:2](=[O:6])[NH:13][N:15]=1)([CH3:12])[CH3:11]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 112513-Methyl-2-butanoneHCID 15620607Glyoxylic acid, monohydrateHCID 44558531Aminoammonium hydroxide

생성물 2

HCID 230281476-Isopropyl-3-pyridazinoneHCID 595491404-Hydroxy-5,5,6-trimethyl-4,5-dihydropyridazin-3(2H)-one

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

7.1 A mixture of 14.4 g (157 mmol) of glyoxylic acid monohydrate and 50 ml (464 mmol) of isopropyl methyl ketone is heated at 120° C. with stirring for two hours. The reaction mixture is cooled to 40° C., and 70 ml of water and 12 ml of 32% aqueous ammonia solution are added. This mixture is extracted three times with dichloromethane. 7.55 ml (155 mmol) of hydrazinium hydroxide are added to the aqueous phase, and the mixture is heated at reflux for 18 hours. The reaction mixture is cooled to room temperature and extracted with dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with petroleum ether/tert-butyl methyl ether as eluent, giving 4-hydroxy-5,5,6-trimethyl-4,5-dihydro-2H-pyridazin-3-one as colourless crystals (ESI 157) and 6-isopropyl-2H-pyridazin-3-one as colourless crystals (ESI 139).

후처리

  1. temperatureThe reaction mixture is cooled to 40° C.
  2. extractionThis mixture is extracted three times with dichloromethane
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 18 hours
  5. temperatureThe reaction mixture is cooled to room temperature
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated
  9. customThe residue is chromatographed on a silica-gel column with petroleum ether/tert-butyl methyl ether as eluent

출처 및 근거

ORD 기록
ord-114b1f76192349a18d6fceeb5801be28
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557813B2

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