Reaction #42445

Reaction equation

methyl 4-methyl-3,5-dinitrobenzoate

dimethylformamide dimethyl acetal

→

title compound

Yield 99.5%

Methyl 4-[(E)-2-(dimethylamino)ethenyl]-3,5-dinitrobenzoate

Yield 99.5%

Solvents

toluene

Conditions

Workup

1. 1
   Otherremoved
2. 2
   Temperaturefrom heat
3. 3
   Temperaturecooled to room temperature
4. 4
   OtherThe solvents were removed under reduced pressure at which time hexanes
5. 5
   workup.ADDITIONwas added to the residue
6. 6
   Filtrationthe residue was filtered

Procedure

To a mixture of methyl 4-methyl-3,5-dinitrobenzoate (5.6 g) in toluene (20 mL) was added dimethylformamide dimethyl acetal (4.17 g) and 5-sulfo salycylic acid hydrate (0.1 g). The mixture was heated to 110° C. for 19 h, removed from heat and cooled to room temperature. The solvents were removed under reduced pressure at which time hexanes was added to the residue and the residue was filtered to give 6.85 g of the title compound: 1H NMR (CDCl3) δ 2.97, 3.96, 5.54, 6.74, 8.33.

Source