1-Ethenyl-4-methoxy-9H-pyrido[3,4-b]indol-8-ol

Base Information

• Chemical Name: 1-Ethenyl-4-methoxy-9H-pyrido[3,4-b]indol-8-ol
• CAS No.: 100234-59-1
• Molecular Formula: C₁₄H₁₂N₂O₂
• Molecular Weight: 240.261
• Mol file: 100234-59-1.mol

Synonyms:PicrasidineI;1-Ethenyl-4-methoxy-9H-b-carbolin-8-ol;4-Methoxy-1-vinyl-9H-b-carbolin-8-ol;

Chemical Property of 1-Ethenyl-4-methoxy-9H-pyrido[3,4-b]indol-8-ol

Chemical Property:

• Boiling Point: 528.2 °C at 760 mmHg
• Flash Point: 273.3 °C
• PSA: 58.14000
• Density: 1.352 g/cm³
• LogP: 3.07330

Purity/Quality:

99% ^*data from raw suppliers

PicrasidineI 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Ethenyl-4-methoxy-9H-pyrido[3,4-b]indol-8-ol

There total 12 articles about 1-Ethenyl-4-methoxy-9H-pyrido[3,4-b]indol-8-ol 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: 79.0%

4-Methoxy-8-tosyloxy-1-vinyl-β-carboline (245662-13-9) → picrasidine I (100234-59-1)

Guidance literature:

With sodium anthracenide; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

Reference yield:

Ethyl 7-tosyloxyindole-2-carboxylate (126260-57-9) → picrasidine I (100234-59-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / DIBAL-H / CH₂Cl₂ / 0.08 h / -78 °C

2.1: 89 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

3.1: 79 percent / Et₃N; NaBH₃CN / methanol / 24 h / 20 °C

4.1: 100 percent / HCOOH / 24 h / 20 °C

5.1: 80 percent / MsOH / 8 h / 55 °C

6.1: p-TsOH / benzene / 0.5 h / 20 °C

6.2: 70 percent / chloranil / benzene / 12 h / 20 °C

7.1: 98 percent / MCPBA / CH₂Cl₂ / 24 h / 20 °C

8.1: 65 percent / Et₃N / 1,2-dichloro-ethane / 2 h / 80 °C

9.1: 80 percent / HCl / 5 h / Heating

10.1: 80 percent / DIBAL-H / CH₂Cl₂ / 0.08 h / -50 °C

11.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 20 °C

11.2: 49 percent / tetrahydrofuran; hexane / 2 h / 70 °C

12.1: 79 percent / sodium anthracenide / tetrahydrofuran / 0.08 h / 0 °C

With hydrogenchloride; manganese(IV) oxide; n-butyllithium; formic acid; methanesulfonic acid; sodium anthracenide; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; benzene; 1.1: Reduction / 2.1: Oxidation / 3.1: Condensation / 4.1: Formylation / 5.1: Cyclization / 6.1: Substitution / 6.2: Oxidation / 7.1: Oxidation / 8.1: Substitution / 9.1: Substitution / 10.1: Reduction / 11.1: Elimination / 11.2: Wittig reaction / 12.1: Reduction;

Reference yield:

7-Tosyloxyindole-2-carbaldehyde (245662-02-6) → picrasidine I (100234-59-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 79 percent / Et₃N; NaBH₃CN / methanol / 24 h / 20 °C

2.1: 100 percent / HCOOH / 24 h / 20 °C

3.1: 80 percent / MsOH / 8 h / 55 °C

4.1: p-TsOH / benzene / 0.5 h / 20 °C

4.2: 70 percent / chloranil / benzene / 12 h / 20 °C

5.1: 98 percent / MCPBA / CH₂Cl₂ / 24 h / 20 °C

6.1: 65 percent / Et₃N / 1,2-dichloro-ethane / 2 h / 80 °C

7.1: 80 percent / HCl / 5 h / Heating

8.1: 80 percent / DIBAL-H / CH₂Cl₂ / 0.08 h / -50 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 20 °C

9.2: 49 percent / tetrahydrofuran; hexane / 2 h / 70 °C

10.1: 79 percent / sodium anthracenide / tetrahydrofuran / 0.08 h / 0 °C

With hydrogenchloride; n-butyllithium; formic acid; methanesulfonic acid; sodium anthracenide; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; benzene; 1.1: Condensation / 2.1: Formylation / 3.1: Cyclization / 4.1: Substitution / 4.2: Oxidation / 5.1: Oxidation / 6.1: Substitution / 7.1: Substitution / 8.1: Reduction / 9.1: Elimination / 9.2: Wittig reaction / 10.1: Reduction;

upstream raw materials:

4-Methoxy-8-tosyloxy-1-vinyl-β-carboline

Ethyl 7-tosyloxyindole-2-carboxylate

7-Tosyloxyindole-2-carbaldehyde

7-Tosyloxyindole-2-methanol

Downstream raw materials:

dehydrocrenatidine

Refernces