1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one

Base Information

• Chemical Name: 1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one
• CAS No.: 886754-60-5
• Molecular Formula: C₂₀H₂₀ClN₃O
• Molecular Weight: 353.851

Synonyms:1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one

Chemical Property of 1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one

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Technology Process of 1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one

There total 2 articles about 1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one 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: 44.0%

1-amino-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one (401834-53-5) + 4-chlorobenzaldehyde (104-88-1) → 1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one (886754-60-5)

Guidance literature:

With piperidine; In ethanol; for 2h; Heating;

DOI:10.1016/j.tet.2006.01.054

Reference yield:

1-carbamoylmethyl-2,3,3-trimethyl-3H-indolinium chloride (90907-07-6) → 1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one (886754-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / hydrazine dihydrate / 0.5 h / 70 °C

2: 44 percent / piperidine / ethanol / 2 h / Heating

With piperidine; hydrazine hydrate; In ethanol;

DOI:10.1016/j.tet.2006.01.054

Reference yield: 26.0%

1-{[(1E)-(4-chlorophenyl)methylene]amino}-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one (886754-60-5) → N'-[(1E)-(4-chlorophenyl)methylene]-2-(2,3,3-trimethyl-2,3-dihydro-1H-indol-1-yl)acetohydrazide

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 70 ℃; for 1h;

DOI:10.1016/j.tet.2006.01.054

upstream raw materials:

1-amino-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazolo[1,2-a]indol-2(9H)-one

4-chlorobenzaldehyde

1-carbamoylmethyl-2,3,3-trimethyl-3H-indolinium chloride

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