3-Nitrobenzaldehyde → HCID 19871254, compound

HRID 329860Notes

Reaction equation

HRID 329860 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]=[CH:29][N:28]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:33]/[C:34](/[CH3:40])=[CH:35]\[C:36]([O:38][CH3:39])=[O:37]>C(O)(C)C>[CH3:40][C:34]1[NH:33][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH2:23][CH2:22]2)=[O:17])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:35]=1[C:36]([O:38][CH3:39])=[O:37]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 198712182-[4-(Pyridin-2-yl)piperazin-1-yl]ethyl 3-oxobutanoate

Product 1

HCID 19871254HCID 19871254, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-nitrobenzaldehyde, 2-[4-(2-pyridyl)-1-piperazinyl)ethyl acetoacetate and methyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1 to give methyl 2-[4-(2-pyridyl)-1-piperazinyl]ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 53°-56° C. (sintering). Yield 54.5%. IR(Nujol)cm-1 : 3280. NMR(CDCl3) δ: 2.35(3H,s, ##STR34## 2.37(3H,s, ##STR35## 3.64(3H,s,COOCH3), 4.21(2H,t,J=6,COOCH2CH2 --), 5.13(1H,s, C(4) --H), 5.77(1H,s,NH).

Sources & evidence

ORD record
ord-891e4fc1717349ceb3b466752fd10ae2
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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