HRID2235338

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81184

1,8-Diazabicyclo[5.4.0]undec-7-ene

C9H16N2

$结构：CC/C=C\CBr$

HCID6110173

(2Z)-1-Bromo-2-pentene

C5H9Br

结构：CC(=O)Nc1cc2c(cc1[N+](=O)[O-])NC(=O)C2(C)C

HCID23092658

N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

C12H13N3O4

HCID23665647

2-Methyl-2-propanol, potassium salt

C4H9KO

PRODUCTS

生成物

$结构：CC/C=C\CN1C(=O)C(C)(C)c2cc(N)c([N+](=O)[O-])cc21$

HCID59300902

未命名化合物

收率 38.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1.47 g) is alkylated using (Z)-1-bromo-2-pentene (1 g; 6.71 mmol) and KOtBu (0.75 g; 6.71 mmol) at RT for 20 h. After aqueous work-up and flash chromatography on silica gel eluting with light petroleum/EtOAc (2.5:1) the pure alkylated acetamide (0.85 g; 2.56 mmol) is de-acetylated under reflux conditions using DBU (0.7 ml) in MeOH (60 ml). (Z)-5-amino-3,3-dimethyl-6-nitro-1-(pent-2-enyl)-1,3-dihydro-indol-2-one (0.62 g) is obtained after aqueous work-up.

WORKUP

后处理

customat RT
customfor 20 h