isolysergic acid

Base Information

• Chemical Name: isolysergic acid
• CAS No.: 478-95-5
• Molecular Formula: C16H16 N2 O2
• Molecular Weight: 268.315
• Mol file: 478-95-5.mol

Synonyms:Ergoline-8a-carboxylic acid,9,10-didehydro-6-methyl- (8CI); Isolysergic acid (6CI,7CI); Indolo[4,3-fg]quinoline,ergoline-8-carboxylic acid deriv.; D-Isolysergic acid

Chemical Property of isolysergic acid

Chemical Property:

• Vapor Pressure: 2.51E-12mmHg at 25°C
• Melting Point: 218° (dec)
• Refractive Index: 1.6240 (estimate)
• Boiling Point: 536.2°C at 760 mmHg
• PKA: 3.44, pKb 8.61(at 25℃)
• Flash Point: 278.1°C
• PSA: 56.33000
• Density: 1.39g/cm³
• LogP: 2.06010

Purity/Quality:

99%, ^*data from raw suppliers

ISOLYSERGIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of isolysergic acid

There total 2 articles about isolysergic acid 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:

lysergic acid sulfate (88133-12-4) → 6-methyl-9,10-didehydro-ergoline-8-carboxylic acid (478-95-5) + D-lysergic acid (82-58-6)

Guidance literature:

With ammonia; In methanol; water; Product distribution / selectivity;

Reference yield:

N-[(7-methyl-6,6a,7,8-tetrahydro-4H-indolo[4,3-fg]quinolin-9-ylidene)-(toluene-4-sulfonyl)-methyl]-formamide (764710-82-9) → 6-methyl-9,10-didehydro-ergoline-8-carboxylic acid (478-95-5) + D-lysergic acid (82-58-6)

Guidance literature:

With hydrogenchloride; for 0.5h; Title compound not separated from byproducts; Heating;

DOI:10.1021/jo049209b

Reference yield: 79.0%

(+/-)-lysergic acid (82-58-6,478-95-5,6915-32-8,23953-76-6,68985-97-7,68985-98-8) → rac-9,10-dihydrolysergic acid (2481-70-1,5878-43-3,6838-23-9,6871-64-3)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/j.bmcl.2007.12.030

upstream raw materials:

N-[(7-methyl-6,6a,7,8-tetrahydro-4H-indolo[4,3-fg]quinolin-9-ylidene)-(toluene-4-sulfonyl)-methyl]-formamide

lysergic acid sulfate

Downstream raw materials:

(+/-)-isolysergic acid hydrazide

methyl (6aRS,9RS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate

methyl (6aRS,9SS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate

D-lysergic acid

Refernces

• 1、 Moldvai, Istvan,Temesvari-Major, Eszter,Incze, Maria,Szentirmay, Eva,Gacs-Baitz, Eszter,Szantay, Csaba. "Enantioefficient synthesis of α-ergocryptine: First direct synthesis of (+)-lysergic acid". . p. 5993 - 6000. Retrieved 2007/10/03.