Dimethylformamide dimethyl acetal → (E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

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A solution of methyl 4-methyl-3-nitrobenzoate (4.46 g) in N,N-dimethylformamide (23 ml) was treated with N,N-dimethylformamide dimethyl acetal (8.18 g) and heated at 130° for 2 hours. The solvent was evaporated and the residue was triturated with ether to give methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (5.58 g, 98%) as a red powder; NMR (80 MHz, CDCl3): 2.98[s, 6H, N(CH3)2 ], 5.90(d, 1H, CHN), 7.14(d, 1H, CHCHN), 7.45(d, 1H, H5 -Ar), 7.90(dd, 1H, H6 -Ar), 8.47(d, 1H, H2 -Ar).

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