5-[(4-bromo-2,5-dimethoxyanilino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Base Information

• Chemical Name: 5-[(4-bromo-2,5-dimethoxyanilino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS No.: 133400-93-8
• Molecular Formula: C₁₅H₁₆BrNO₆
• Molecular Weight: 386.199
• Mol file: 133400-93-8.mol

Synonyms:5-<<(4-bromo-2,5-dimethoxyphenyl)amino>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione

Chemical Property of 5-[(4-bromo-2,5-dimethoxyanilino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Chemical Property:

Purity/Quality:

5-[(4-Bromo-2,5-dimethoxyanilino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione ^*data from reagent suppliers

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Technology Process of 5-[(4-bromo-2,5-dimethoxyanilino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

There total 1 articles about 5-[(4-bromo-2,5-dimethoxyanilino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-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: 95.0%

5-{[(2,5-dimethoxyphenylamino)]methylidene}-2,2-dimethyl-4,6-dioxo-1,3-dioxane (97545-51-2) → 5-<<(4-bromo-2,5-dimethoxyphenyl)amino>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione (133400-93-8)

Guidance literature:

With bromine; In acetic acid; at 23 ℃; for 30h;

DOI:10.1021/jo00011a011

Reference yield:

5-<<(4-bromo-2,5-dimethoxyphenyl)amino>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione (133400-93-8) → 6-bromo-4-<2-<(trifluoroacetyl)amino>-phenyl>quinoline-5,8-dione (133400-91-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / diphenyl ether / 0.33 h / 250 - 260 °C

2: 92 percent / 4-(dimethylamino)pyridine, 2,6-dimethylpyridine / CH₂Cl₂ / 12 h / 23 °C

3: 64 percent / LiCl, Cu(I)Br, tetrakis(triphenylphosphine)palladium / dioxane / 60 h / 90 °C

4: 100 percent / trifluoroacetic acid / 2 h / 23 °C

5: 48 percent / ammonium cerium(IV) nitrate, 2M H₂SO₄ / acetonitrile / 16 h / 23 °C

With 2,6-dimethylpyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium cerium(IV) nitrate; sulfuric acid; trifluoroacetic acid; lithium chloride; copper(I) bromide; In 1,4-dioxane; diphenylether; dichloromethane; acetonitrile;

DOI:10.1021/jo00011a011

Reference yield:

5-<<(4-bromo-2,5-dimethoxyphenyl)amino>methylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione (133400-93-8) → 6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline (133400-98-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / diphenyl ether / 0.33 h / 250 - 260 °C

2: 92 percent / 4-(dimethylamino)pyridine, 2,6-dimethylpyridine / CH₂Cl₂ / 12 h / 23 °C

3: 64 percent / LiCl, Cu(I)Br, tetrakis(triphenylphosphine)palladium / dioxane / 60 h / 90 °C

With 2,6-dimethylpyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; copper(I) bromide; In 1,4-dioxane; diphenylether; dichloromethane;

DOI:10.1021/jo00011a011

upstream raw materials:

5-{[(2,5-dimethoxyphenylamino)]methylidene}-2,2-dimethyl-4,6-dioxo-1,3-dioxane

Downstream raw materials:

6-bromo-4-<2-<(trifluoroacetyl)amino>-phenyl>quinoline-5,8-dione

6-bromo-4-<2-(tert-butoxycarbonyl)amino>-5,8-dimethoxyquinoline

6-bromo-5,8-dimethoxy-4-<2-<(trifluoroacetyl)amino>-phenyl>quinoline

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