Reaktion #53363

Reaktionsgleichung

(±)-7-methyl-5-(4-nitrophenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isochromen-6-ylium perchlorate

ethyl acetate

perchloric acid

2-hydrazinopyrimdine

→

title compound

Ausbeute 64.0%

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

Ausbeute 64.0%

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 1 h
2. 2
   Filtrationwas filtered off
3. 3
   Einengenconcentrated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
5. 5
   Waschenwashed several times with water
6. 6
   SonstigeAfter drying
7. 7
   Sonstigeevaporation the crude product
8. 8
   Sonstigewas purified by column chromatography
9. 9
   workup.ADDITIONa mixture of toluene-ethyl acetate (0.1:4) as eluent

Vorschrift

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.

Quelle