Methyl 3-formylbenzoate → HCID 70351527, compound

HRID 329874Notes

Reaction equation

HRID 329874 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=O)=[O:4].[C:13]([O:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH:28]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)(=[O:18])[CH2:14][C:15]([CH3:17])=O.[NH2:43]/[C:44](/[CH3:51])=[CH:45]\[C:46]([O:48][CH2:49][CH3:50])=[O:47]>C(O)(C)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:8]2[C:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[C:44]([CH3:51])[NH:43][C:15]([CH3:17])=[C:14]2[C:13]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH:28]([C:29]3[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=3)[C:36]3[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=3)[CH2:24][CH2:23]2)=[O:18])[CH:10]=[CH:11][CH:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 639145Methyl 3-formylbenzoateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 19871204HCID 19871204, compound

Product 1

HCID 70351527HCID 70351527, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of m-methoxycarbonylbenzaldehyde, 2-[4-(4,4'-dimethylbenzhydryl)-1-piperazinyl]ethyl acetoacetate and ethyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1 to give 2-[4-(4,4'-dimethylbenzhydryl)-1-piperazinyl]ethyl ethy 4-(3-methoxycarbonylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 80°-83° C. (sintering). Yield 47.5%. IR(Nujol)cm-1 : 3330, 1720, 1690. NMR(CDCl3) δ: 1.17(3H,t,J=7,--CH2CH3), 2.25(6H,s, ##STR49## 2.31(6H,s, ##STR50## 3.83(3H,s,--COOCH3), 4.03(2H, q,J=7,--CH2CH3), 4.10(1H,s,>N--CH<), 4.10(2H,t,J=6, --COOCH2CH2 --), 5.00(1H,s,C(4) --H), 5.78(1H,broad s, NH).

Sources & evidence

ORD record
ord-27cd96607b9c416dabb5d2655fd50f8f
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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