Reacción #322447

Ecuación de reacción

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

Rendimiento 9.1%

Disolventes

oxychloride

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente