3-Nitrobenzaldehyde → HCID 19871232, compound

HRID 329857Notes

Reaction equation

HRID 329857 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]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:37]/[C:38](/[CH3:44])=[CH:39]\[C:40]([O:42][CH3:43])=[O:41]>C(O)(C)C>[CH3:44][C:38]1[NH:37][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[CH2:25][CH2:26]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:39]=1[C:40]([O:42][CH3:43])=[O:41]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 19871223HCID 19871223, compound

Product 1

HCID 19871232HCID 19871232, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-nitrobenzaldehyde, 2-[4-(3-trifluoromethylphenyl)-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-(3-trifluoromethylphenyl)-1-piperazinyl]ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 95°-87° C. (sintering). Yield 82.7%. IR(Nujol)cm-1 : 3345, 1695, 1645. NMR(CDCl3) δ: 2.34(6H,s, ##STR31## 3.64(3H,s,COOCH3), 4.21(2H,t,J=5.5,--COOCH2CH2 --), 5.11(1H,s,C(4) --H), 6.39(1H,s,NH).

Sources & evidence

ORD record
ord-a8fe9f3c937541ada8cb66622cef3c7a
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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