3-Nitrobenzaldehyde → HCID 19871226, compound

HRID 329856Notes

Reaction equation

HRID 329856 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].[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:34]/[C:35](/[CH3:41])=[CH:36]\[C:37]([O:39][CH3:40])=[O:38]>C(O)(C)C>[CH3:16][C:14]1[NH:34][C:35]([CH3:41])=[C:36]([C:37]([O:39][CH3:40])=[O:38])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:13]=1[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[CH2:23][CH2:22]1)=[O:17]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 198712082-[4-(3-Chlorophenyl)piperazin-1-yl]ethyl 3-oxobutanoate

Product 1

HCID 19871226HCID 19871226, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-nitrobenzaldehyde, 2-[4-(3-chlorophenyl)-1-piperazinyl]ethyl acetoacetate and methyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1 to give 2-[4-(3-chlorophenyl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 65°-68° C. (sintering). Yield 29.0%. IR(Nujol)cm-1 : 3300. NMR(CDCl3) δ: 2.34(3H,s, ##STR29## 2.36(3H,s, ##STR30## 3.63(3H,s,COOCH3), 4.21(2H,t,J=6,--COOCH2CH2 --), 5.12(1H,s,C(4) --H), 5.89(1H,s,NH).

Sources & evidence

ORD record
ord-4ae6f2a3f1584a7482d8587187bdac86
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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