4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

Base Information

Chemical Name:4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione
CAS No.:174866-35-4
Molecular Formula:C₂₁H₁₆N₂O₄
Molecular Weight:360.369
Hs Code.:

Synonyms:4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

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Chemical Property of 4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

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Technology Process of 4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

There total 2 articles about 4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione 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: 89.0%

: 62-53-3
aniline

: 174866-34-3
2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

: 149-73-5
trimethyl orthoformate

: 174866-35-4
4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

Guidance literature:: With acetic acid; In N,N-dimethyl-formamide; at 90 ℃; for 3.5h;
DOI:10.1021/jo9518415

Reference yield:

: 28281-86-9
4,5-methylenedioxyhomophthalic anhydride

: 174866-35-4
4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 79 percent / CH₂Cl₂ / 20 h / Ambient temperature

2: 89 percent / AcOH / dimethylformamide / 3.5 h / 90 °C

With acetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9518415

Reference yield:

: 174866-35-4
4-(anilinomethylene)-2-(3-butynyl)-6,7-(methylenedioxy)-1,2,3,4-tetrahydroisoquinoline-1,3-dione

: 40360-71-2
anhydrolycorine-7-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) t-BuOK, 2.) 36percent HCl, 3.) HCl, pH 4 / 1.) DMF, 90 deg C, 1 h, 2.) room temperature, 3 h, 3.) MeOH, overnight

2: 83 percent / nitrobenzene / 7 h / Heating

3: 1.) KOH, 2.) Cu bronze / 1.) EtOH, 80 deg C, 15 min, 2.) quinoline, 220 deg C, 2.5 h

With hydrogenchloride; potassium hydroxide; copper bronze; potassium tert-butylate; In nitrobenzene;
DOI:10.1021/jo9518415