4,5-DIHYDRO-1H-BENZO[E][1,4]DIAZEPIN-2(3H)-ONE

Base Information

• Chemical Name: 4,5-DIHYDRO-1H-BENZO[E][1,4]DIAZEPIN-2(3H)-ONE
• CAS No.: 1824-72-2
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.191
• Hs Code.: 2933990090
• Mol file: 1824-72-2.mol

Synonyms:4,5-DIHYDRO-1H-BENZO[E][1,4]DIAZEPIN-2(3H)-ONE

Chemical Property of 4,5-DIHYDRO-1H-BENZO[E][1,4]DIAZEPIN-2(3H)-ONE

Chemical Property:

• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.547
• Boiling Point: 365.6 °C at 760 mmHg
• Flash Point: 173.1 °C
• PSA: 41.13000
• Density: 1.137 g/cm³
• LogP: 1.19510

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,5-Dihydro-1H-benzo[e][1,4]diazepin-2(3H)-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,5-DIHYDRO-1H-BENZO[E][1,4]DIAZEPIN-2(3H)-ONE

There total 11 articles about 4,5-DIHYDRO-1H-BENZO[E][1,4]DIAZEPIN-2(3H)-ONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tert-butyl 2-oxo-1,2,3,5-tetrahydro-4H-1,4-benzodiazepine-4-carboxylate (179686-66-9) → 1,3,4,5-tetrahydro-2H-benzo[e][1,4]diazepin-2-one (1824-72-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

C17H16N2O3 → 1,3,4,5-tetrahydro-2H-benzo[e][1,4]diazepin-2-one (1824-72-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.5b00074

Reference yield:

2-nitrophenylmethyl bromide (3958-60-9) → 1,3,4,5-tetrahydro-2H-benzo[e][1,4]diazepin-2-one (1824-72-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / water; 1,4-dioxane / 10 h / 0 - 20 °C

3.1: iron / methanol / 70 °C

3.2: 2 h / Reflux

4.1: lithium hydroxide / water; tetrahydrofuran / 10 h / 20 °C

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 0 °C

5.2: 1 h / 20 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; iron; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/acsmedchemlett.5b00074

upstream raw materials:

1-methyl-2-nitrobenzene

2-nitrophenylmethyl bromide

methyl N-(2-nitrobenzyl)glycinate

methyl N-(tert-butoxycarbonyl)-N-(2-nitrobenzyl)glycinate

Downstream raw materials:

2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine

Refernces

• 1、 Jiang, Tao,Zhou, Yuren,Chen, Zhuxi,Sun, Peng,Zhu, Jianming,Zhang, Qiang,Wang, Zhen,Shao, Qiang,Jiang, Xiangrui,Li, Bo,Chen, Kaixian,Jiang, Hualiang,Wang, Heyao,Zhu, Weiliang,Shen, Jingshan. "Design, synthesis, and pharmacological evaluation of fused β-homophenylalanine derivatives as potent DPP-4 inhibitors". . p. 602 - 606. Retrieved 2015/05/27.