Hydroxyevodiamine

Base Information

• Chemical Name: Hydroxyevodiamine
• CAS No.: 1238-43-3
• Molecular Formula: C19H17N3O2
• Molecular Weight: 319.363
• Mol file: 1238-43-3.mol

Synonyms:(13bR)-8,13,13b,14-Tetrahydro-13bα-hydroxy-14-methylindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one;

Chemical Property of Hydroxyevodiamine

Chemical Property:

• Melting Point: 195℃ (dec.) (ethanol )
• Boiling Point: 618.4 °C at 760 mmHg
• Flash Point: 327.8 °C
• PSA: 59.57000
• Density: 1.48 g/cm³
• LogP: 3.02330

Purity/Quality:

≥98% ^*data from raw suppliers

Hydroxyevodiamine >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Hydroxyevodiamine is an alkaloid with potential cytotoxicity against the proliferation of cancer cells.

Technology Process of Hydroxyevodiamine

There total 14 articles about Hydroxyevodiamine 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:

isatoic anhydride (118-48-9) → 13b-hydroxyevodiamine (1238-43-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.17 h

1.2: 16 h / 45 °C

2.1: dichloromethane / Heating

3.1: potassium permanganate / acetone / 3 h / 60 °C

4.1: hydrogenchloride / dichloromethane; isopropyl alcohol / 0.25 h / 20 °C

5.1: aq. phosphate buffer / 24 h / 20 °C / pH 8.5

With hydrogenchloride; potassium permanganate; N-ethyl-N,N-diisopropylamine; In aq. phosphate buffer; dichloromethane; N,N-dimethyl acetamide; isopropyl alcohol; acetone;

DOI:10.1016/j.tet.2016.03.059

Reference yield:

tryptamine (61-54-1) → 13b-hydroxyevodiamine (1238-43-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydrogencarbonate; water / dichloromethane / 2 h / 0 °C

2.1: boron trifluoride diethyl etherate / toluene / 0 °C / Reflux

3.1: trichlorophosphate / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere

3.2: 96 h / 75 °C / Inert atmosphere

4.1: hydrogenchloride / dichloromethane; isopropyl alcohol / 0.25 h / 20 °C

5.1: aq. phosphate buffer / 24 h / 20 °C / pH 8.5

With hydrogenchloride; boron trifluoride diethyl etherate; water; sodium hydrogencarbonate; trichlorophosphate; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; isopropyl alcohol; toluene;

DOI:10.1016/j.tet.2016.03.059

Reference yield:

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → 13b-hydroxyevodiamine (1238-43-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 12 h / 45 °C

2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.17 h

2.2: 16 h / 45 °C

3.1: dichloromethane / Heating

4.1: potassium permanganate / acetone / 3 h / 60 °C

5.1: hydrogenchloride / dichloromethane; isopropyl alcohol / 0.25 h / 20 °C

6.1: aq. phosphate buffer / 24 h / 20 °C / pH 8.5

With hydrogenchloride; potassium permanganate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; N,N-dimethyl acetamide; isopropyl alcohol; acetone;

DOI:10.1016/j.tet.2016.03.059

upstream raw materials:

3,4-dihydro-β-carboline

isatoic anhydride

tryptamine

(2-(1H-indol-3-yl)ethyl)carbamic acid phenyl ester

Downstream raw materials:

N-Methylanthranilic acid

Refernces