Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-

Base Information

• Chemical Name: Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-
• CAS No.: 53462-75-2
• Molecular Formula: C10H8N2O
• Molecular Weight: 172.18
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30201644
• Nikkaji Number: J72.950G
• Wikidata: Q83074840
• Pharos Ligand ID: BLFRAJRZ38AB
• ChEMBL ID: CHEMBL356104
• Mol file: 53462-75-2.mol

Synonyms:53462-75-2;Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-;BRN 0880614;3,4-Dihydropyrrolo[4,3,2-de]isoquinolin-5(1H)-one;CHEMBL356104;3,4-Dihydropyrrolo(4,3,2-de)isoquinolin-5(1H)-one;5-24-03-00467 (Beilstein Handbook Reference);SCHEMBL743601;3,4-Dihydro-1H-pyrrolo[4,3,2-de]isoquinolin-5-one;DTXSID30201644;PYLXNOZFJZQGBX-UHFFFAOYSA-N;BDBM50120703;LS-139426;3,4-dihydropyrrolo[4,3,2-de]isoquinolin5(lH)-one;3,4-Dihydropyrrolo[4,3,2-de]isoquinolin-5(lH)-one;3,4-Dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-one;5-oxo-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]isoquinoline;2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraen-7-one

Chemical Property of Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-

Chemical Property:

• Vapor Pressure: 5.52E-11mmHg at 25°C
• Boiling Point: 521.8°C at 760 mmHg
• Flash Point: 269.4°C
• PSA: 48.38000
• Density: 1.394g/cm³
• LogP: 1.42170
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 172.063662883
• Heavy Atom Count: 13
• Complexity: 241

Purity/Quality:

3,4-DIHYDRO-PYRROLO[4,3,2-DE]ISOQUINOLIN-5(1H)-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CNC3=CC=CC(=C23)C(=O)N1

Technology Process of Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-

There total 9 articles about Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro- 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: 81.0%

3-(Aminomethyl)indole-4-carboxylic Acid Methyl Ester (57280-91-8) → 3,4-dihydro-1H-pyrrolo[4,3,2-de]isoquinolin-5-one (53462-75-2)

Guidance literature:

With sodium methylate; In methanol;

Reference yield: 61.0%

4-methylidene-5-nitro-3,4-dihydro-2H-isoquinolin-1-one (851659-71-7) → 3,4-dihydro-1H-pyrrolo[4,3,2-de]isoquinolin-5-one (53462-75-2)

Guidance literature:

With carbon monoxide; 1,3-bis-(diphenylphosphino)propane; 1,10-phenanthroline hydrate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide; for 26.5h; under 4560 Torr; Heating;

DOI:10.1016/j.tet.2005.02.033

Reference yield:

2-bromo-3-nitro-N-(2-propen-1-yl)benzamide (851659-70-6) → 3,4-dihydro-1H-pyrrolo[4,3,2-de]isoquinolin-5-one (53462-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / Pd(OAc)2; tri(o-tolyl)phosphine; triethylamine / 79.5 h / 20 - 120 °C

2: 61 percent / CO; dppp; 1,10-phenanthroline monohydrate / Pd(dba)2 / dimethylformamide / 26.5 h / 4560 Torr / Heating

With palladium diacetate; carbon monoxide; 1,3-bis-(diphenylphosphino)propane; 1,10-phenanthroline hydrate; triethylamine; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.02.033

upstream raw materials:

4-methylidene-5-nitro-3,4-dihydro-2H-isoquinolin-1-one

2-bromo-3-nitro-N-(2-propen-1-yl)benzamide

2-bromo-3-nitrobenzoic acid chloride

2-bromo-3-nitro-benzoic acid

Downstream raw materials:

1-(phenylsulfonyl)-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5(1H)-one

1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]isoquinoline

1-(phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline

4-methyl-1-(phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline

Refernces

• 1、 S?derberg, Bj?rn C.G.,Hubbard, Jeremiah W.,Rector, Stacey R.,O'Neil, Shannon N.. "Synthesis of fused indoles by sequential palladium-catalyzed Heck reaction and N-heteroannulation". . p. 3637 - 3649. Retrieved 2007/10/03.
• 2、 -. "Certain 4,6-dihydropyrrolotriazoline-quinoline derivatives". . . Retrieved 2008/06/13.