Hydroxyamine hydrochloride → 7-Bromo-4-(N-hydroxy-imino)-1-(2-pyridyl)-3,6,6-trimethyl-4,5,6,7-tetrahydroindazole

HRID 2084286

반응식

HRID 2084286 반응식
[Br:1][CH:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[N:8]=[C:7]([CH3:17])[C:6]=2[C:5](=O)[CH2:4][C:3]1([CH3:20])[CH3:19].Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>O1CCOCC1>[Br:1][CH:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[N:8]=[C:7]([CH3:17])[C:6]=2[C:5](=[N:22][OH:23])[CH2:4][C:3]1([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochloride2회HCID 517045Sodium Acetate2회HCID 40739867-Bromo-3,6,6-trimethyl-1-pyridin-2-yl-5,7-dihydroindazol-4-one

생성물 1

HCID 571058077-Bromo-4-(N-hydroxy-imino)-1-(2-pyridyl)-3,6,6-trimethyl-4,5,6,7-tetrahydroindazole수율 45%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture of 7-bromo-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazole (0.3 g, 0.9 mmol), prepared as described in example 4, hydroxylamine hydrochloride (0.37 g, 4.5 mmol), and sodium acetate (0.44 g, 5.4 mmol) in 1,4-dioxane (50 ml) was heated under reflux for about 4 hours. Additional hydroxylamine hydrochloride (0.123 g, 1.6 eq) and sodium acetate (0.146 g, 2 eq) were added and heating was continued for further 4 hours. The reaction mixture was poured onto ice/water and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel (cyclohexane:ethyl acetate=90:10) to give the title compound as a colourless solid (0.14 g, 45%): m.p. 195-196° C.

후처리

  1. customprepared
  2. temperaturewas heated
  3. temperatureunder reflux for about 4 hours
  4. temperatureheating
  5. additionThe reaction mixture was poured onto ice/water
  6. extractionextracted with dichloromethane
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe residue was chromatographed on silica gel (cyclohexane:ethyl acetate=90:10)

출처 및 근거

ORD 기록
ord-8fa14da4604641c0ae2faca3d132a82c
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716856B1

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