N⁴-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine

Base Information

• Chemical Name: N⁴-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine
• CAS No.: 102781-03-3
• Molecular Formula: C₂₄H₂₈F₃N₃O₃
• Molecular Weight: 463.5

Synonyms:N⁴-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine

Chemical Property of N⁴-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine

Chemical Property:

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Technology Process of N⁴-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine

There total 8 articles about N⁴-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine 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: 87.0%

8-<(4'-amino-1-methylbutyl)amino>-5,6-dimethoxy-4-<methyl>quinoline phthalimidate (102781-02-2) → N4-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine (102781-03-3)

Guidance literature:

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

DOI:10.1021/jm00159a042

Reference yield:

2-(4-iodopentyl)-1,3-isoindolinedione (63460-47-9) → N4-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine (102781-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / Et₃N / dimethylformamide / 5 h / 85 - 90 °C

2: 87 percent / hydrazine / ethanol / 2 h / Heating

With triethylamine; hydrazine; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00159a042

Reference yield:

4-methyl-5,6-dimethoxy-8-nitroquinoline (64992-96-7) → N4-[5,6-Dimethoxy-4-(3-trifluoromethyl-phenoxymethyl)-quinolin-8-yl]-pentane-1,4-diamine (102781-03-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) selenium dioxide, acetic anhydride, acetic acid, 2.) 3N HCl / 1.) dioxane, reflux, 2h, 2.) THF, reflux, 20 min

2: 1.) phenol, triethylsilane, 2.) TFAA / 1.) water, 8 deg C, 2.) water, 30 deg C, overnight

3: phosphorus oxychloride / CH₂Cl₂ / 1 h / Heating

4: 57 percent / dimethylformamide / 1 h / 55 - 60 °C

5: 75 percent / 1.3 N HCl, Sn, stannous chloride / tetrahydrofuran; ethanol / 0.5 h / 8 °C

6: 54 percent / Et₃N / dimethylformamide / 5 h / 85 - 90 °C

7: 87 percent / hydrazine / ethanol / 2 h / Heating

With hydrogenchloride; triethylsilane; tin; selenium(IV) oxide; acetic anhydride; acetic acid; triethylamine; trifluoroacetic anhydride; tin(ll) chloride; hydrazine; trichlorophosphate; phenol; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00159a042

upstream raw materials:

8-<(4'-amino-1-methylbutyl)amino>-5,6-dimethoxy-4-<methyl>quinoline phthalimidate

2-(4-iodopentyl)-1,3-isoindolinedione

4-methyl-5,6-dimethoxy-8-nitroquinoline

5,6-dimethoxy-8-nitroquinoline-4-carboxaldehyde

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