8-((2-Chloropropionyl)amino)-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one

Base Information

• Chemical Name: 8-((2-Chloropropionyl)amino)-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one
• CAS No.: 121866-04-4
• Molecular Formula: C₁₅H₁₆ClN₃O₂
• Molecular Weight: 305.764
• DSSTox Substance ID: DTXSID10923998
• ChEMBL ID: CHEMBL73122
• Mol file: 121866-04-4.mol

Synonyms:BRN 6528287;2-Chloro-N-(2,3,4,4a,5,6-hexahydro-3-oxobenzo(h)cinnolin-8-yl)propanamide;8-((2-Chloropropionyl)amino)-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one;Propanamide, 2-chloro-N-(2,3,4,4a,5,6-hexahydro-3-oxobenzo(h)cinnolin-8-yl)-;121866-04-4;CHEMBL73122;DTXSID10923998;C15-H16-Cl-N3-O2;LS-119082;2-Chloro-N-(3-hydroxy-4,4a,5,6-tetrahydrobenzo[h]cinnolin-8-yl)propanamide

Chemical Property of 8-((2-Chloropropionyl)amino)-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one

Chemical Property:

• Density: 1.48g/cm³
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 305.0931045
• Heavy Atom Count: 21
• Complexity: 480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)NC1=CC2=C(C=C1)C3=NNC(=O)CC3CC2)Cl

Technology Process of 8-((2-Chloropropionyl)amino)-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one

There total 5 articles about 8-((2-Chloropropionyl)amino)-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-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: 72.0%

2-chloropropionyl chloride (7623-09-8) + dl-8-amino-4,4a,5,6-tetrahydro-2H-benzo(h)-cinnolin-3-one (103422-66-8) → 8-[(2-chloropropionyl)amino]-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one (121866-04-4)

Guidance literature:

In toluene; for 6h; Heating;

DOI:10.1021/jm00130a009

Reference yield:

8-Acetylamino-4,4a,5,6-tetrahydrobenzocinnolin-3(2H)-one (103602-95-5,103602-97-7,103422-56-6,121866-03-3) → 8-[(2-chloropropionyl)amino]-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one (121866-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 4 N HCl / 2 h / 100 °C

2: 72 percent / toluene / 6 h / Heating

With hydrogenchloride; In toluene;

DOI:10.1021/jm00130a009

Reference yield:

6-(acetylamino)-1,2,3,4-tetrahydro-1-oxo-2-naphthalenideneacetic acid (103602-85-3) → 8-[(2-chloropropionyl)amino]-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one (121866-04-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / Zn, AcOH / H₂O / 0.5 h / 100 °C

2: 91 percent / H₂NNH₂*H₂O / ethanol / 3 h / Heating

3: 85 percent / 4 N HCl / 2 h / 100 °C

4: 72 percent / toluene / 6 h / Heating

With hydrogenchloride; hydrazine hydrate; acetic acid; zinc; In ethanol; water; toluene;

DOI:10.1021/jm00130a009

upstream raw materials:

2-chloropropionyl chloride

dl-8-amino-4,4a,5,6-tetrahydro-2H-benzo(h)-cinnolin-3-one

8-Acetylamino-4,4a,5,6-tetrahydrobenzocinnolin-3(2H)-one

6-(acetylamino)-1,2,3,4-tetrahydro-1-oxo-2-naphthalenideneacetic acid