Reacción #322445

Ecuación de reacción

N-methylformanilide

2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one

→

9-formyl-2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one

Rendimiento 59.4%

Disolventes

oxychloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring at room temperature for 2 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
   OtroThe residue was chromatographed on a silica gel column
8. 8
   OtroThe solid was recrystallized from a mixed solvent of ethanol and ethyl acetate

Procedimiento

A mixture of 4.7 g of N-methylformanilide in 3.3 ml of phosphrus oxychloride was stirred at room temperature for an hour and 5.4 g of 2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one was added thereto. After stirring at room temperature for 2 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 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 ethanol and ethyl acetate to give 3.5 g of 9-formyl-2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one as a pale brown powder, melting at 127°-129° C.

Fuente