1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid

Base Information

Chemical Name:1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid
CAS No.:853021-77-9
Molecular Formula:C₃₃H₃₈N₂O₃
Molecular Weight:510.676
Hs Code.:

Synonyms:1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid

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Chemical Property of 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid

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Technology Process of 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid

There total 11 articles about 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid 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: 72.0%

: 853021-76-8
ethyl 1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylate

: 853021-77-9
1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid

Guidance literature:: With sodium hydroxide; In ethanol; water; for 2h; Heating;
DOI:10.1016/j.tet.2005.02.041

Reference yield:

: 853021-69-9
ethyl 8-iodo-1,2,3,4-tetrahydroquinoline-6-carboxylate

: 853021-77-9
1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / triethylamine; bis(triphenylphosphine)palladium dichloride; copper(I) iodide / 1 h / 0 °C

2.1: 70 percent / palladium dichloride / acetonitrile / 16 h / Heating

3.1: diethyl ether / 1 h / 20 °C

3.2: 95 percent / tetrahydrofuran / 20 °C

4.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

4.2: 42 percent / N,N-dimethylethanolamine / methanol / 3 h / Heating

5.1: 72 percent / NaOH / ethanol; H₂O / 2 h / Heating

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; borane-THF; triethylamine; palladium dichloride; In tetrahydrofuran; diethyl ether; ethanol; water; acetonitrile; 1.1: Sonogashira coupling;
DOI:10.1016/j.tet.2005.02.041

Reference yield:

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 853021-77-9
1-{N-[4-(4-methoxyphenyl)but-1-yl]aminoethyl}-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-8-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: 60 percent / N-bromosuccinimide / CCl₄ / 3 h / 20 °C

2.1: 60 percent / dimethylformamide / 16 h / Heating

3.1: 95 percent / hydrogen peroxide; NaOH / H₂O / 24 h / Heating

4.1: 60 percent / HCl / H₂O / 72 h / Heating

5.1: 60 percent / iodine monochloride; calcium carbonate / methanol; H₂O / 0 - 20 °C

6.1: 92 percent / triethylamine; bis(triphenylphosphine)palladium dichloride; copper(I) iodide / 1 h / 0 °C

7.1: 70 percent / palladium dichloride / acetonitrile / 16 h / Heating

8.1: diethyl ether / 1 h / 20 °C

8.2: 95 percent / tetrahydrofuran / 20 °C

9.1: BH₃*THF / tetrahydrofuran / 3 h / Heating

9.2: 42 percent / N,N-dimethylethanolamine / methanol / 3 h / Heating

10.1: 72 percent / NaOH / ethanol; H₂O / 2 h / Heating

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; N-Bromosuccinimide; copper(l) iodide; borane-THF; dihydrogen peroxide; Iodine monochloride; triethylamine; calcium carbonate; palladium dichloride; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetonitrile; 6.1: Sonogashira coupling;
DOI:10.1016/j.tet.2005.02.041