2,3-Dichlorobenzaldehyde → HCID 19871256, compound

HRID 329853Notes

Reaction equation

HRID 329853 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH:26]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:22][CH2:21]1)(=[O:16])[CH2:12][C:13]([CH3:15])=O.[NH2:41]/[C:42](/[CH3:48])=[CH:43]\[C:44]([O:46][CH3:47])=[O:45]>C(O)(C)C>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:43]([C:44]([O:46][CH3:47])=[O:45])=[C:42]([CH3:48])[NH:41][C:13]([CH3:15])=[C:12]1[C:11]([O:17][CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][N:23]([CH:26]([C:34]2[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=2)[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:24][CH2:25]1)=[O:16]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 19871203HCID 19871203, compound

Product 1

HCID 19871256HCID 19871256, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2,3-dichlorobenzaldehyde, 2-[4-(4,4'-dichlorobenzhydryl)-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-(4,4'-dichlorobenzhydryl)-1-piperazinyl]ethyl methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate as a light yellow powder, m.p. 104°-107° C. (sintering). Yield 43.2%. IR(KBr)cm-1 : 3340, 1695. NMR(CDCl3) δ: 2.27(6H,s, ##STR25## 3.57(3H,s,COOCH3), 4.12(2H,t,J=6,--COOCH2CH2 --), 4.18(1H,s,>N--CH<), 5.43(1H,s,C(4) --H), 5.70(1H,broad s, NH).

Sources & evidence

ORD record
ord-ff416529da16469fbd9401c29df07049
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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