Dimethylformamide dimethyl acetal → (E)-methyl 4-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-methyl-3,5-dinitrobenzoate (D162) (20 g, 83.3 mmol, 1 equiv) in DMF (30 ml) was added N,N-dimethylformamide dimethylacetal (35 ml, excess) and the resulting solution was stirred at 45° C. for 30 min then cooled to room temperature and concentrated in vacuo. Trituration of the residue with Et2O/iso-hexane gave methyl 4-[(E)-2-(dimethylamino)ethenyl]-3,5-dinitrobenzoate (D200) (20 g, 81%) as a dark red solid which was used in the next step without further purification.

Provenance & Evidence