Reaktion #322447

Reaktionsgleichung

N-methylformanilide

2-(4-methylphenyl)-5,6-dihydrothieno-[2,3-h]cinnolin-3(2H)-one

→

8-hydroxymethyl-2-(4-methylphenyl)-5,6-dihydrothieno-[2,3-h]cinnolin3(2H)-one

Ausbeute 9.1%

Lösungsmittel

oxychloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring at room temperature for 10 hours
2. 2
   workup.ADDITIONthe mixture was poured into ice-cold water
3. 3
   Extraktionextracted with chloroform
4. 4
   WaschenThe extract was washed with water
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   workup.DISSOLUTIONThe residue was dissolved in methanol
8. 8
   workup.ADDITION1.0 g of sodium borohydride was added
9. 9
   Temperaturunder ice-cooling
10. 10
    workup.STIRRINGAfter stirring for an hour
11. 11
    workup.ADDITIONthe mixture was poured into diluted hydrochloric acid
12. 12
    Extraktionextracted with chloroform
13. 13
    WaschenThe extract was washed with brine
14. 14
    Trocknendried over anhydrous magnesium sulfate
15. 15
    Einengenconcentrated in vacuo
16. 16
    SonstigeThe residue was chromatographed on a silica gel column
17. 17
    SonstigeThe solid was recrystallized from a mixed solvent of isopropyl alcohol and isopropyl ether

Vorschrift

A mixture of 1.9 g of N-methylformanilide in 1.3 ml of phosphrus oxychloride was stirred at room temperature for an hour and 2.0 g of 2-(4-methylphenyl)-5,6-dihydrothieno-[2,3-h]cinnolin-3(2H)-one was added thereto. After stirring at room temperature for 10 hours, the mixture was poured into ice-cold water and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was dissolved in methanol and 1.0 g of sodium borohydride was added thereto under ice-cooling. After stirring for an hour, the mixture was poured into diluted hydrochloric acid and extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1) as an eluent. The solid was recrystallized from a mixed solvent of isopropyl alcohol and isopropyl ether to give 0.2 g of 8-hydroxymethyl-2-(4-methylphenyl)-5,6-dihydrothieno-[2,3-h]cinnolin3(2H)-one as a brown powder, melting at 166°-169° C.

Quelle