3-Nitrobenzaldehyde → 2,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-benzyloxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][C:21](=[O:26])[CH2:22][C:23]([CH3:25])=O)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27]/[C:28](/[CH3:34])=[CH:29]\[C:30]([O:32][CH3:33])=[O:31].[N+:35]([C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[CH:41]=O)([O-:37])=[O:36]>>[CH3:34][C:28]1[NH:27][C:23]([CH3:25])=[C:22]([C:21]([O:20][CH2:19][CH2:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:14]=2)=[O:26])[CH:41]([C:40]2[CH:43]=[CH:44][CH:45]=[C:38]([N+:35]([O-:37])=[O:36])[CH:39]=2)[C:29]=1[C:30]([O:32][CH3:33])=[O:31]Participants
Procedure
The ω-phenylalkylacetoacetate derivative (5) is then reacted with an alkyl β-aminocrotonate (or methoxyethyl β-aminocrotonate depending on the desired R5) and a benzaldehyde derivative (depending on the desired R4, e.g. for compounds in which R4 is meta --NO2, 3-nitrobenzaldehyde is used) under Hantzsch Dihydropyridine synthesis conditions (see, e.g., Fox, et al., J. Org. Chem., 16, 1259 (1951)) to form a 4-phenyl-2,5-dimethyl-1,4-dihydropyridine dicarboxylate diester (6). For example, 2-[4-(2-benzyloxyethoxy)phenyl]ethylacetoacetate (5) is reacted with methyl β-aminocrotonate and 3-nitrobenzaldehyde to produce 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-benzyloxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine (Step 6).
Sources & evidence
- ORD record
- ord-8c9aaa9eed7b4664a9dd94ae460fb8e0
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04672071
Reaction notes
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