3-Nitrobenzaldehyde → HCID 19871196, compound

HRID 329849Notes

Reaction equation

HRID 329849 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH3:12][O:13][C:14]1[CH:43]=[CH:42][C:17]([CH:18]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][O:35][C:36](=[O:41])[CH2:37][C:38]([CH3:40])=O)[CH2:29][CH2:28]2)[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:16][CH:15]=1.[NH2:44]/[C:45](/[CH3:51])=[CH:46]\[C:47]([O:49][CH3:50])=[O:48]>C(O)(C)C>[CH3:40][C:38]1[NH:44][C:45]([CH3:51])=[C:46]([C:47]([O:49][CH3:50])=[O:48])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:37]=1[C:36]([O:35][CH2:34][CH2:33][N:30]1[CH2:29][CH2:28][N:27]([CH:18]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:43][CH:42]=2)[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:32][CH2:31]1)=[O:41]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 19871197HCID 19871197, compound

Product 1

HCID 19871196HCID 19871196, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-nitrobenzaldehyde, 2-[4-(4,4'-dimethoxybenzhydryl)-1-piperazinyl]ethylacetoacetate and methyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1 to give 2-[4-(4,4'-dimethoxybenzhydryl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 76°-80° C. (sintering). Yield 39.3%. IR(Nujol)cm-1 : 3330, 1695, 1680(shoulder). NMR(CDCl3) δ: 2.36(6H,s, ##STR21## 3.57(3H,s,--COOCH3), 3.75(6H,s,OCH3), 4.11(1H,s,>N--CH<), 4.15(2H,t,J=6, --COOCH2CH2 --), 5.08(1H,s,C(4) --H), 5.80(1H,broad s, NH).

Sources & evidence

ORD record
ord-fca36b34e72a40b19a17d747dcb8ffd4
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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