4-Nitrobenzaldehyde → Ethyl 3-(4-aminophenyl)acrylate

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Reaction Steps

The above approach could be used to convert 4-nitrobenzaldehyde (Aldrich) into 3-(4-nitrophenyl)propenoic acid ethyl ester. The latter compound could be reduced (J. Am. Chem. Soc., 1944, 66, 1442) to give 3-(4-aminophenyl)propenoic acid ethyl ester. Reaction of (4-aminophenyl)-propenoic acid ethyl ester with an omega-haloalkyl-isocyanate provides an 4-(omega-haloalkylaminocarbonyl)aminophenyl)propenoic acid ethyl ester (see., Khim. Farm. Zh. 1984, 18(12), 1432-1436). The latter compound can be reacted with sodium hydride to give a 4-(1,3-diaza-2-oxoalicyclylphenyl)propenoic acid ethyl ester (see., Bioorg. Med. Chem. Lett. 1999, 9(5), 749-754), the latter compound could be converted to give a 3-(4-(1,3-diaza-2-oxoalicycl-1-yl)phenyl)propenoic acid ethyl ester by the methods described in Bioorg. Med. Chem. Lett. 1999, 9(5), 749-754. The latter compound could be elaborated by methods described previously, to give a 3-(4-(1,3-diaza-2-oxoalicycl-1-yl)phenyl)-3-amino propanoic acid ethyl ester suitable for subsequent coupling.

Provenance & Evidence