HRID621537

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID222

Ammonia gas

H3N

HCID11776829

2-[Methyl(phenylmethyl)amino]ethyl 3-oxobutanoate

C14H19NO3

结构：CC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(=O)OCC1CC1

HCID53956239

未命名化合物

PRODUCTS

生成物

结构：CC1=C(C(=O)OCCN(C)Cc2ccccc2)C(c2cccc([N+](=O)[O-])c2)C(C(=O)OCC2CC2)=C(C)N1

HCID3065914

未命名化合物

收率 42.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

A mixture of 4.0 g (16 mmol) of 2-(N-benzyl-N-methylamino)ethyl acetoacetate, 4.6 g (16 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate, 1.12 ml of 28% aqueous ammonia and 40 ml of ethanol was stirred at the reflux temperature for 8 hours, and then the solvent was removed under reduced pressure. The residue was chromatographed on silica gel column to afford 3-cyclopropylmethyl 5-[2-(N-benzyl-N-methylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (3.5 g, 42.1%) as yellow oil. Treatment of this oil with hydrochloric acid gave the corresponding salt.

WORKUP

后处理

customthe solvent was removed under reduced pressure
customThe residue was chromatographed on silica gel column

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-54e3911edb1240338130292957529339
来源数据集: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04824855
来源说明: uspto-grants-1989_04

反应 SMILES

[C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:19]([C:22]1[CH:23]=[C:24]([CH:37]=[CH:38][CH:39]=1)[CH:25]=[C:26]([C:34]([CH3:36])=O)[C:27]([O:29][CH2:30][CH:31]1[CH2:33][CH2:32]1)=[O:28])([O-:21])=[O:20].[NH3:40]>C(O)C>[CH3:36][C:34]1[NH:40][C:3]([CH3:5])=[C:2]([C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:11])=[O:6])[CH:25]([C:24]2[CH:37]=[CH:38][CH:39]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:26]=1[C:27]([O:29][CH2:30][CH:31]1[CH2:33][CH2:32]1)=[O:28]