isoquinolin-4-yl 4-methylbenzenesulfonate

Base Information

• Chemical Name: isoquinolin-4-yl 4-methylbenzenesulfonate
• CAS No.: 1532-82-7
• Molecular Formula: C16H13NO3S
• Molecular Weight: 299.35
• Mol file: 1532-82-7.mol

Synonyms:Toluol-4-sulfonsaeure-[4]isochinolylester;4-Tosyloxy-isochinolin;4-tosyloxyisoquinoline;

Chemical Property of isoquinolin-4-yl 4-methylbenzenesulfonate

Chemical Property:

• PSA: 64.64000
• LogP: 4.39170

Purity/Quality:

95% ^*data from raw suppliers

4-(4-Methylbenzenesulfonate)-4-isoquinolinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(4-Methylbenzenesulfonate)-4-isoquinolinol is an impurity of 1-Phenyl-2,3-dihydroisoquinolin-4(1H)-one Hydrochloride (P309050), which is a useful synthetic intermediate in the synthesis of cis-Hydroxy Solifenacin (H953525) and cis-Hydroxy Solifenacin N-Oxide (H953485); both metabolites of Solifenacin (S676700, HCl) which is a muscarinic M3 receptor antagonist and is used in treatment of urinary incontinence.

Technology Process of isoquinolin-4-yl 4-methylbenzenesulfonate

There total 6 articles about isoquinolin-4-yl 4-methylbenzenesulfonate 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: 66.0%

isoquinoline N-oxide (1532-72-5) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid-[4]isoquinolyl ester (1532-82-7)

Guidance literature:

With potassium carbonate; In 1,2-dichloro-ethane; at 100 ℃; for 12h; regioselective reaction; Schlenk technique;

DOI:10.1002/cctc.201600555

Reference yield:

4-aminoisoquinoline (23687-25-4) → toluene-4-sulfonic acid-[4]isoquinolyl ester (1532-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrochloric acid; water / Diazotization_.Erhitzen der Diazoniumsalz-Loesung mit wss. Schwefelsaeure und Harnstoff

2: pyridine

With pyridine; hydrogenchloride; water;

Reference yield:

isoquinoline N-oxide (1532-72-5) → toluene-4-sulfonic acid-[4]isoquinolyl ester (1532-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid anhydride; water

2: pyridine

With pyridine; water; acetic anhydride;

upstream raw materials:

isoquinoline N-oxide

chloroform

p-toluenesulfonyl chloride

4-isoquinolinol

Downstream raw materials:

2-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-isoquinolinium; chloride

4-isoquinolinol

1-isoquinolone