7-Aminonitrazepam

Base Information

• Chemical Name: 7-Aminonitrazepam
• CAS No.: 4928-02-3
• Molecular Formula: C15H13N3O
• Molecular Weight: 251.288
• European Community (EC) Number: 641-746-2
• UNII: 1A49O337AZ
• DSSTox Substance ID: DTXSID20197749
• Nikkaji Number: J274.741C
• Wikidata: Q27252146
• Metabolomics Workbench ID: 49559
• ChEMBL ID: CHEMBL147144
• Mol file: 4928-02-3.mol

Synonyms:7-aminonitrazepam

Chemical Property of 7-Aminonitrazepam

Chemical Property:

• Vapor Pressure: 5.73E-10mmHg at 25°C
• Melting Point: 242-244oC
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 495.8°C at 760 mmHg
• PKA: pKa 2.5 4.6 13.1(5%MeOH in H2O t=20 I=0.15) (Uncertain)
• Flash Point: 253.6°C
• PSA: 67.48000
• Density: 1.3g/cm³
• LogP: 2.21310
• Storage Temp.: -20°C Freezer
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 251.105862047
• Heavy Atom Count: 19
• Complexity: 374

Purity/Quality:

99% ^*data from raw suppliers

7-Aminonitrazepam solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant? ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)NC2=C(C=C(C=C2)N)C(=N1)C3=CC=CC=C3
• Uses: A metabolite of Nitrazepam (N490140).

Technology Process of 7-Aminonitrazepam

There total 4 articles about 7-Aminonitrazepam 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: 91.0%

nitrazepam (146-22-5) → 7-amino-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one (4928-02-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 1h; under 1520.1 Torr;

DOI:10.1016/j.bmc.2008.04.059

Reference yield:

N-(2-benzoyl-4-nitrophenyl)-2-chloroacetamide (20821-91-4) → 7-amino-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one (4928-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hexamethylenetetramine; ammonium acetate / ethanol / 6 h / 78 °C

2: tin(II) chloride dihdyrate / ethanol / 2 h / 20 °C / Sonication

With tin(II) chloride dihdyrate; hexamethylenetetramine; ammonium acetate; In ethanol;

DOI:10.1002/cbdv.202000342

Reference yield:

2-amino-5-nitrobenzophenone (1775-95-7) → 7-amino-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one (4928-02-3)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 2 h / 110 °C / Inert atmosphere

2: hexamethylenetetramine; ammonium acetate / ethanol / 6 h / 78 °C

3: tin(II) chloride dihdyrate / ethanol / 2 h / 20 °C / Sonication

With tin(II) chloride dihdyrate; hexamethylenetetramine; ammonium acetate; In ethanol; toluene;

DOI:10.1002/cbdv.202000342

upstream raw materials:

nitrazepam

N-(2-benzoyl-4-nitrophenyl)-2-chloroacetamide

2-amino-5-nitrobenzophenone

Downstream raw materials:

7-[(E)-benzylideneamino]-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

7-{(E)-[(4-nitrophenyl)methylidene]amino}-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

7-[(E)-{[4-(dimethylamino)phenyl]methylidene}amino]-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Refernces

• 1、 Severino, Beatrice,Fiorino, Ferdinando,Perissutti, Elisa,Frecentese, Francesco,Cirino, Giuseppe,Roviezzo, Fiorentina,Santagada, Vincenzo,Caliendo, Giuseppe. "Synthesis and pharmacological evaluation of peptide-mimetic protease-activated receptor-1 antagonists containing novel heterocyclic scaffolds". . p. 6009 - 6020. Retrieved 2008/12/21.
• 2、 Beyer,Sadée. "Synthesis and analysis of possible nitrazepam-metabolites. 4. Chemistry and analysis of benzodiazepin-derivatives". . p. 152 - 157. Retrieved 2007/10/05.