bauerine C

Base Information

• Chemical Name: bauerine C
• CAS No.: 156312-11-7
• Molecular Formula: C₁₂H₈Cl₂N₂O
• Molecular Weight: 267.114
• Mol file: 156312-11-7.mol

Synonyms:Bauerine C

Chemical Property of bauerine C

Chemical Property:

• Vapor Pressure: 2.9E-12mmHg at 25°C
• Melting Point: 254-258 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 552.8°Cat760mmHg
• PKA: 11.63±0.20(Predicted)
• Flash Point: 288.1°C
• PSA: 37.79000
• Density: 1.56g/cm³
• LogP: 3.32660

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of bauerine C

There total 5 articles about bauerine C 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: 61.0%

7,8-dichloro-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (945491-42-9) → Bauerine C (156312-11-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20 ℃; for 2h;

DOI:10.1080/00397910701575426

Reference yield:

3-(2,3-piperidinedione)-(2,3-dichlorophenyl)hydrazone → Bauerine C (156312-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / anhydrous formic acid / 24 h / 80 °C

2: 79 percent / potassium tert-butylate / dimethylsulfoxide / 0.5 h / 80 °C

3: 43 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / tetrahydrofuran / 12 h / Heating

With formic acid; potassium tert-butylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dimethyl sulfoxide; 1: Fischer cyclization;

DOI:10.1080/00397910701226228

Reference yield:

3-carboxy-2-piperidone (41888-21-5) → Bauerine C (156312-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: conc. HCl; sodium nitrite / H₂O / 0.17 h / 0 - 5 °C

1.2: 7.8 g / NaHCO₃; acetic acid / H₂O / 8 h / 20 °C / pH 4

2.1: 61 percent / anhydrous formic acid / 24 h / 80 °C

3.1: 79 percent / potassium tert-butylate / dimethylsulfoxide / 0.5 h / 80 °C

4.1: 43 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / tetrahydrofuran / 12 h / Heating

With hydrogenchloride; formic acid; potassium tert-butylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; In tetrahydrofuran; water; dimethyl sulfoxide; 1.2: Japp-Klingemann reaction / 2.1: Fischer cyclization;

DOI:10.1080/00397910701226228

upstream raw materials:

7,8-dichloro-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one

3-carboxy-2-piperidone

7,8-dichloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one

3-carboethoxy-2-pyridone

Refernces

• 1、 Pohl, Berthold,Luchterhandt, Thomas,Bracher, Franz. "Total syntheses of the chlorinated β-carboline alkaloids bauerine A, B, and C". . p. 1273 - 1280. Retrieved 2008/02/01.