HRID1906474

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7449

3-Nitrobenzaldehyde

C7H5NO3

HCID14923

Ammonium hydroxide

H5NO

HCID11403106

未命名化合物

PRODUCTS

生成物

结构：CC1=C(C(=O)OCCN2C(=O)c3ccccc3C2=O)C(c2cccc([N+](=O)[O-])c2)C(C(=O)OCCN2C(=O)c3ccccc3C2=O)=C(C)N1

HCID13799832

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID3776

Isopropanol

C3H8O

PROCEDURE

实验过程

A solution of 137 mg (0.9 m mol) of 3-nitrobenzaldehyde, 0.5 g (1.82 m mol) of 2-phthalimidoethyl acetoacetate, and 0.16 ml (2.4 m mol) of 14.7M ammonium hydroxide in 40 ml of 2-propanol was refluxed for 15 hours under nitrogen. The solvent was removed in vacuo and the residue was subjected to flash chromatography (silica gel, 3:1 petroleum ether/ethyl acetate) to yield 50 mg of pale yellow product; m.p. 92°-94° C.; NMR: (CDCl3) δ2.2 (6M,s), 3.8 (4H,m), 4.2 (4H,m), 4.8 (1H,s), 6.1 (1H,s), 7.2 (12H,m).

WORKUP

后处理

customThe solvent was removed in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-865a44a1094442cba37ac10515e4a6eb
来源数据集: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04652573
来源说明: uspto-grants-1987_03

反应 SMILES

[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[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])(=[O:17])[CH2:13][C:14]([CH3:16])=O.[OH-:32].[NH4+:33]>CC(O)C>[CH3:16][C:14]1[NH:33][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH2:19][CH2:20][N:21]2[C:22](=[O:31])[C:23]3=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]3[C:25]2=[O:26])=[O:32])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:13]=1[C:12]([O:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])=[O:17]