ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate

Base Information

• Chemical Name: ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate
• CAS No.: 956586-36-0
• Molecular Formula: C₂₁H₂₂N₂O₅
• Molecular Weight: 382.416

Synonyms:ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate

Chemical Property of ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate

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Technology Process of ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate

There total 5 articles about ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate 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: 77.0%

ethyl 2-[4',6'-dimethoxy-3'-(4''-methylphenyl)indol-2'-yl]glyoxylate (956586-31-5) → ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate (956586-36-0)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; In ethanol; for 7h; Heating;

DOI:10.1016/j.tet.2007.08.026

Reference yield:

4-(bromoacetyl)toluene (619-41-0) → ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate (956586-36-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydrogen carbonate / ethanol / 4 h / Heating

2.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 1 h / 20 °C

2.2: trifluoroacetic acid / 0.25 h / Heating

2.3: sodium hydroxide / methanol / 1 h

3.1: diethyl ether / 3 h / 20 °C

3.2: 44 percent / 2 h

4.1: 77 percent / hydroxylamine hydrochloride; sodium acetate / ethanol / 7 h / Heating

With hydroxylamine hydrochloride; sodium acetate; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; ethanol;

DOI:10.1016/j.tet.2007.08.026

Reference yield:

3.5-dimethoxyaniline (10272-07-8) → ethyl 4',6'-dimethoxy-3'-(4''-methylphenyl)-indol-2'-yl-2-(hydroxyimino)acetate (956586-36-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydrogen carbonate / ethanol / 4 h / Heating

2.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 1 h / 20 °C

2.2: trifluoroacetic acid / 0.25 h / Heating

2.3: sodium hydroxide / methanol / 1 h

3.1: diethyl ether / 3 h / 20 °C

3.2: 44 percent / 2 h

4.1: 77 percent / hydroxylamine hydrochloride; sodium acetate / ethanol / 7 h / Heating

With hydroxylamine hydrochloride; sodium acetate; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; ethanol;

DOI:10.1016/j.tet.2007.08.026

upstream raw materials:

ethyl 2-[4',6'-dimethoxy-3'-(4''-methylphenyl)indol-2'-yl]glyoxylate

4,6-dimethoxy-3-(4-methylphenyl)-1H-indole

4-(bromoacetyl)toluene

3.5-dimethoxyaniline

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