(E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide

Base Information

• Chemical Name: (E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide
• CAS No.: 1417639-11-2
• Molecular Formula: C₂₀H₁₉N₃O₃
• Molecular Weight: 349.389
• Mol file: 1417639-11-2.mol

Synonyms:(E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide

Chemical Property of (E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide

There total 3 articles about (E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide 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: 18.0%

3-amino-4-hydroxy-N,N-dimethylbenzamide (176429-16-6) + trans-3-indole-acrylic acid (1204-06-4,29953-71-7) → (E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide (1417639-11-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201206691

Reference yield:

3-nitro-4-hydroxybenzoic acid (616-82-0) → (E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide (1417639-11-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine / acetonitrile

2: hydrogen; 5%-palladium/activated carbon / methanol

3: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With 5%-palladium/activated carbon; hydrogen; benzotriazol-1-ol; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201206691

Reference yield:

C9H10N2O4 (176429-17-7) → (E)-3-[3-(1H-indol-3-yl)acrylamido]-4-hydroxy-N,N-dimethylbenzamide (1417639-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; 5%-palladium/activated carbon / methanol

2: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With 5%-palladium/activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.201206691

upstream raw materials:

3-nitro-4-hydroxybenzoic acid

C₉H₁₀N₂O₄

3-amino-4-hydroxy-N,N-dimethylbenzamide

trans-3-indole-acrylic acid