N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine

Base Information

Chemical Name:N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine
CAS No.:1567847-63-5
Molecular Formula:C₂₁H₂₂ClN₃
Molecular Weight:351.879
Hs Code.:

Synonyms:N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine

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Chemical Property of N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine

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Technology Process of N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine

There total 11 articles about N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine 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: 14.0%

: 1567847-57-7
1-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-N-ethyl-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-9-carboxamide

: 1567847-58-8
5-(4-chlorophenyl)-N-ethyl-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-9-carboxamide

: 1567847-63-5
N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Reflux;
DOI:10.1016/j.ejmech.2013.12.008

Reference yield:

: 1567847-49-7
ethyl 1-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-9-carboxylate

: 1567847-63-5
N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium hydroxide / methanol / 24 h / Reflux

2.1: triethylamine; chloroformic acid ethyl ester / dichloromethane / 0.5 h / 0 °C

2.2: 72 h / 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux

With lithium aluminium tetrahydride; chloroformic acid ethyl ester; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.ejmech.2013.12.008

Reference yield:

: 131667-57-7
tert-butyl 1,2,3,4-tetrahydro-1-pyridinecarboxylate

: 1567847-63-5
N-{{5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methyl}ethanamine

Guidance literature:: Multi-step reaction with 5 steps

1.1: scandium tris(trifluoromethanesulfonate) / acetonitrile / 0.08 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 72 h / 20 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 20 °C / Inert atmosphere

3.1: potassium hydroxide / methanol / 24 h / Reflux

4.1: triethylamine; chloroformic acid ethyl ester / dichloromethane / 0.5 h / 0 °C

4.2: 72 h / 20 °C

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux

With lithium aluminium tetrahydride; chloroformic acid ethyl ester; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; dichloromethane; chloroform; acetonitrile;
DOI:10.1016/j.ejmech.2013.12.008