Ethyl Acetate → 1-{6-[(4-Nitrophenyl)-(pyrimidin-2-yl-hydrazono)-methyl]-benzo-1,3-dioxol-5-yl}-propan-2-ol

HRID 25085

Reaktionsgleichung

Reaktionsgleichung von HRID 25085
C(OCC)(=O)C.Cl(O)(=O)(=O)=O.Cl([O-])(=O)(=O)=O.[CH3:17][CH:18]1[CH2:27][C:26]2[CH:25]=[C:24]3[O:28][CH2:29][O:30][C:23]3=[CH:22][C:21]=2[CH:20]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)[OH+:19]1.[NH:40]([C:42]1[N:47]=[CH:46][CH:45]=[CH:44][N:43]=1)[NH2:41]>C(O)(C)C>[N+:37]([C:34]1[CH:35]=[CH:36][C:31]([C:20](=[N:41][NH:40][C:42]2[N:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[C:21]2[C:26]([CH2:27][CH:18]([OH:19])[CH3:17])=[CH:25][C:24]3[O:28][CH2:29][O:30][C:23]=3[CH:22]=2)=[CH:32][CH:33]=1)([O-:39])=[O:38]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24247Perchloric AcidHCID 3465582-HydrazinylpyrimidineHCID 131724741(+/-)-7-Methyl-5-(4-nitrophenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isochromen-6-ylium perchlorate

Produkt 1

HCID 865938161-{6-[(4-Nitrophenyl)-(pyrimidin-2-yl-hydrazono)-methyl]-benzo-1,3-dioxol-5-yl}-propan-2-olAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A stirred mixture of 3.29 g (9.99 mmol) of (±)-7-methyl-5-(4-nitrophenyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochroman-5-ol, 40 ml of ethyl acetate and 1.0 ml (1.15 mmol) perchloric acid was refluxed for 1 h. After cooling the precipitated (±)-7-methyl-5-(4-nitrophenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isochromen-6-ylium perchlorate was filtered off, and it was stirred at reflux temperature with 1.6 g (14.55 mmol) of 2-hydrazinopyrimdine in 50 ml of isopropanol for 2 h, then concentrated. The residue was dissolved in dichloromethane and washed several times with water. After drying and evaporation the crude product was purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of toluene-ethyl acetate (0.1:4) as eluent to yield 2.71 g (64%) of the title compound; Mp.: 125-127° C.

Aufarbeitung

  1. temperaturewas refluxed for 1 h
  2. filtrationwas filtered off
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed several times with water
  6. customAfter drying
  7. customevaporation the crude product
  8. customwas purified by column chromatography
  9. additiona mixture of toluene-ethyl acetate (0.1:4) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-7fd80c4ad35640a5957268fc3f7f7d79
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858605B2

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