9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one

Base Information

• Chemical Name: 9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one
• CAS No.: 332359-30-5
• Molecular Formula: C₂₂H₂₂INO₂
• Molecular Weight: 459.327
• Mol file: 332359-30-5.mol

Synonyms:9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one

Chemical Property of 9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one

There total 3 articles about 9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-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: 60.0%

p-methoxybenzyl chloride (824-94-2) + 9-iodo-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one (332359-28-1) → 9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one (332359-30-5)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)01934-1

Reference yield:

7-bromo-3,4-dihydro-2H-naphthalen-1-one (32281-97-3) → 9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one (332359-30-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 30 percent / CsF; Si(OMe)4 / 5 h / 80 °C

2.1: n-butyllithium; tert-butyllithium / tetrahydrofuran / 1 h / -78 °C

2.2: 70 percent / iodine / tetrahydrofuran / 2 h / -78 °C

3.1: 60 percent / KOH / dimethylsulfoxide / 0.5 h / 20 °C

With potassium hydroxide; n-butyllithium; tetramethylorthosilicate; tert.-butyl lithium; cesium fluoride; In tetrahydrofuran; dimethyl sulfoxide; 1.1: Corriu's reaction;

DOI:10.1016/j.tet.2004.03.045

Reference yield:

9-bromo-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one (332359-23-6) → 9-iodo-1-(4-methoxybenzyl)-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one (332359-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; tert-butyllithium / tetrahydrofuran / 1 h / -78 °C

1.2: 70 percent / iodine / tetrahydrofuran / 2 h / -78 °C

2.1: 60 percent / KOH / dimethylsulfoxide / 0.5 h / 20 °C

With potassium hydroxide; n-butyllithium; tert.-butyl lithium; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1016/j.tet.2004.03.045

upstream raw materials:

p-methoxybenzyl chloride

9-iodo-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one

7-bromo-3,4-dihydro-2H-naphthalen-1-one

9-bromo-3-methyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one

Downstream raw materials:

2-(1-(4-methoxybenzyl)-3-methyl-2-oxo-1,2,3,4,5,6-hexahydrobenzo[h]quinolin-9-yl)malonic acid diethyl ester