4-Nitrobenzaldehyde → Ethyl 3-(4-aminophenyl)acrylate
Reaction equation
[N+](C1C=CC(C=O)=CC=1)([O-])=O.[CH2:12]([O:14][C:15](=[O:27])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)[CH3:13]>>[CH2:12]([O:14][C:15](=[O:27])[CH:16]=[CH:17][C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1)[CH3:13]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-e30e62a66b1e443f98de3a3916d16324
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06953802B2
Reaction notes
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