3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one

Base Information

• Chemical Name: 3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one
• CAS No.: 203264-27-1
• Molecular Formula: C₂₃H₁₉ClN₂O₃
• Molecular Weight: 406.868

Synonyms:3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one

Chemical Property of 3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one

Chemical Property:

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Technology Process of 3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one

There total 4 articles about 3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-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:

phthalimide (136918-14-4,85-41-6) → 3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one (203264-27-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / K₂CO₃ / dimethylformamide / 4 h / Heating

2: 96 percent / NaBH₄, conc. HCl / methanol; ethanol / 0.5 h / 10 - 20 °C

3: 1.) SOCl₂, 2.) Et₃N / 1) CH₂Cl₂, 30 min; 2) CH₂Cl₂, 5 min; 3) CH₂Cl₂, 1 h

With hydrogenchloride; sodium tetrahydroborate; thionyl chloride; potassium carbonate; triethylamine; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10359-3

Reference yield:

2-bromobenzoic acid methyl ester (610-94-6) → 3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one (203264-27-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / K₂CO₃ / dimethylformamide / 4 h / Heating

2: 96 percent / NaBH₄, conc. HCl / methanol; ethanol / 0.5 h / 10 - 20 °C

3: 1.) SOCl₂, 2.) Et₃N / 1) CH₂Cl₂, 30 min; 2) CH₂Cl₂, 5 min; 3) CH₂Cl₂, 1 h

With hydrogenchloride; sodium tetrahydroborate; thionyl chloride; potassium carbonate; triethylamine; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10359-3

Reference yield:

methyl 2-((1,3-dioxoisoindolin-2-yl)methyl)benzoate (189949-64-2) → 3-(4-chloroanilino)-2,3-dihydro-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one (203264-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / NaBH₄, conc. HCl / methanol; ethanol / 0.5 h / 10 - 20 °C

2: 1.) SOCl₂, 2.) Et₃N / 1) CH₂Cl₂, 30 min; 2) CH₂Cl₂, 5 min; 3) CH₂Cl₂, 1 h

With hydrogenchloride; sodium tetrahydroborate; thionyl chloride; triethylamine; In methanol; ethanol;

DOI:10.1016/S0040-4020(97)10359-3

upstream raw materials:

4-chloro-aniline

2,3-dihydro-3-hydroxy-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one

phthalimide

2-bromobenzoic acid methyl ester

Downstream raw materials:

3-(4-chloroanilino)-2,3-dihydro-2-(2-carboxybenzyl)-1H-isoindol-1-one

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