(E)-N⁴-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N¹-(benzylidene)semicarbazide

Base Information

• Chemical Name: (E)-N⁴-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N¹-(benzylidene)semicarbazide
• CAS No.: 1428787-49-8
• Molecular Formula: C₃₁H₃₂FN₅O₅
• Molecular Weight: 573.624

Synonyms:(E)-N⁴-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N¹-(benzylidene)semicarbazide

Chemical Property of (E)-N⁴-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N¹-(benzylidene)semicarbazide

Chemical Property:

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Technology Process of (E)-N⁴-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N¹-(benzylidene)semicarbazide

There total 12 articles about (E)-N⁴-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N¹-(benzylidene)semicarbazide 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: 84.9%

N1-(3-fluoro-4-(6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yloxy)phenyl)semicarbazide (1449763-33-0) + benzaldehyde (100-52-7) → (E)-N4-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N1-(benzylidene)semicarbazide (1428787-49-8)

Guidance literature:

With acetic acid; In isopropyl alcohol; Reflux;

DOI:10.1016/j.bmc.2013.06.026

Reference yield:

4-(3-chloropropoxy)-3-methoxyacetophenone (58113-30-7) → (E)-N4-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N1-(benzylidene)semicarbazide (1428787-49-8)

Guidance literature:

Multi-step reaction with 10 steps

1: nitric acid / dichloromethane / 2 h / -10 °C

2: toluene / 110 °C

3: iron / acetic acid / 2 h / 40 - 80 °C

4: acetonitrile / 8 h / 25 - 80 °C

5: trichlorophosphate / acetonitrile / 6 h / Reflux

6: chlorobenzene / 20 h / 140 °C

7: iron; hydrogenchloride / ethanol; water / 2 h / Reflux

8: potassium carbonate / acetone / 3 h / 0 - 20 °C

9: hydrazine hydrate / 1,4-dioxane / Reflux

10: acetic acid / isopropyl alcohol / Reflux

With hydrogenchloride; nitric acid; iron; potassium carbonate; hydrazine hydrate; acetic acid; trichlorophosphate; In 1,4-dioxane; ethanol; dichloromethane; water; acetic acid; chlorobenzene; isopropyl alcohol; acetone; toluene; acetonitrile;

DOI:10.1016/j.bmc.2013.06.026

Reference yield:

1-[4-(3-chloropropoxy)-5-methoxy-2-nitrophenyl]ethan-1-one (1160707-44-7) → (E)-N4-(3-fluoro-4-(6-methoxy-7-(3-(morpholin-4-yl)propoxy)quinoline-4-yloxy)phenyl)-N1-(benzylidene)semicarbazide (1428787-49-8)

Guidance literature:

Multi-step reaction with 9 steps

1: toluene / 110 °C

2: iron / acetic acid / 2 h / 40 - 80 °C

3: acetonitrile / 8 h / 25 - 80 °C

4: trichlorophosphate / acetonitrile / 6 h / Reflux

5: chlorobenzene / 20 h / 140 °C

6: iron; hydrogenchloride / ethanol; water / 2 h / Reflux

7: potassium carbonate / acetone / 3 h / 0 - 20 °C

8: hydrazine hydrate / 1,4-dioxane / Reflux

9: acetic acid / isopropyl alcohol / Reflux

With hydrogenchloride; iron; potassium carbonate; hydrazine hydrate; acetic acid; trichlorophosphate; In 1,4-dioxane; ethanol; water; acetic acid; chlorobenzene; isopropyl alcohol; acetone; toluene; acetonitrile;

DOI:10.1016/j.bmc.2013.06.026

upstream raw materials:

4-(3-chloropropoxy)-3-methoxyacetophenone

1-[4-(3-chloropropoxy)-5-methoxy-2-nitrophenyl]ethan-1-one

N¹-(3-fluoro-4-(6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yloxy)phenyl)semicarbazide

benzaldehyde

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