4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid

Base Information

• Chemical Name: 4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid
• CAS No.: 77405-76-6
• Molecular Formula: C₃₃H₂₇N₃O₁₀
• Molecular Weight: 625.591

Synonyms:4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid

Chemical Property of 4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid

There total 17 articles about 4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic 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: 92.0%

4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-formyl-2-(6-methoxy-5-nitro-quinolin-2-yl)-5-methyl-nicotinic acid (77405-75-5) → 4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid (77405-76-6)

Guidance literature:

With sodium chlorite; aminosulfonic acid; sodium acetate; In 1,4-dioxane; water; for 1.5h; Ambient temperature;

DOI:10.1021/ja00395a071

Reference yield:

2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid (77405-76-6)

Guidance literature:

Multi-step reaction with 11 steps

1: K₂CO₃, KI / dimethylformamide / 14 h / Ambient temperature

2: benzene / 14 h / Heating

3: Na₂S / methanol / 2 h / Heating

4: 96 percent / t-BuOK / toluene; 2-methyl-propan-2-ol / 10 h / Heating

5: 85 percent / TFA / 1 h / 0 °C

6: HNO₃ / nitromethane / 0.42 h / 5 - 20 °C

7: K₂CO₃ / acetone / 5 h / Heating

8: OsO₄, N-methylmorpholine N-oxide, H₂O / acetone; 2-methyl-propan-2-ol / 20 h / Ambient temperature

9: NaIO₄ / dioxane; H₂O / 18 h / 80 °C

10: 74 percent / selenium dioxide, HOAc / 18 h / Heating

11: 92 percent / sodium chlorite, H₂NSO₃H, NaOAc / H₂O; dioxane / 1.5 h / Ambient temperature

With sodium sulfide; sodium chlorite; sodium periodate; osmium(VIII) oxide; selenium(IV) oxide; aminosulfonic acid; potassium tert-butylate; water; nitric acid; sodium acetate; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; potassium iodide; In 1,4-dioxane; methanol; nitromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ja00395a071

Reference yield:

(Z)-3-Amino-1-(2-benzyloxy-3,4-dimethoxy-phenyl)-2-methyl-but-2-en-1-one (92541-05-4) → 4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid (77405-76-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / xylene / 14 h / Heating

2: NaBH₄ / tetrahydrofuran; propan-2-ol / 16 h / Ambient temperature

3: 67 percent / PhPOCl₂ / 3 h / 170 °C

4: 85 percent / dimethylformamide / 14 h / Heating

5: 2.) H₂O, H⁽¹⁺⁾ / 1) C₆H₆, room temperature, 1.5 h

6: 96 percent / t-BuOK / toluene; 2-methyl-propan-2-ol / 10 h / Heating

7: 85 percent / TFA / 1 h / 0 °C

8: HNO₃ / nitromethane / 0.42 h / 5 - 20 °C

9: K₂CO₃ / acetone / 5 h / Heating

10: OsO₄, N-methylmorpholine N-oxide, H₂O / acetone; 2-methyl-propan-2-ol / 20 h / Ambient temperature

11: NaIO₄ / dioxane; H₂O / 18 h / 80 °C

12: 74 percent / selenium dioxide, HOAc / 18 h / Heating

13: 92 percent / sodium chlorite, H₂NSO₃H, NaOAc / H₂O; dioxane / 1.5 h / Ambient temperature

With P,P-dichlorophenylphosphine oxide; sodium chlorite; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; selenium(IV) oxide; aminosulfonic acid; potassium tert-butylate; water; nitric acid; sodium acetate; hydrogen cation; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; nitromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; xylene; tert-butyl alcohol;

DOI:10.1021/ja00395a071

upstream raw materials:

4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-formyl-2-(6-methoxy-5-nitro-quinolin-2-yl)-5-methyl-nicotinic acid

2-nitro-5-hydroxybenzaldehyde

(Z)-3-Amino-1-(2-benzyloxy-3,4-dimethoxy-phenyl)-2-methyl-but-2-en-1-one

4-(4-Methoxy-benzyloxy)-2-[(E)-p-tolylimino-methyl]-phenylamine

Downstream raw materials:

4-(2-Benzyloxy-3,4-dimethoxy-phenyl)-6-(6-methoxy-5-nitro-quinolin-2-yl)-3-methyl-pyridine-2,5-dicarboxylic acid 2-methyl ester

methyl 5-amino-4-<2-(benzyloxy)-3,4-dimethoxyphenyl>-6-(6-methoxy-5-nitro-2-quinolyl)-3-methylpyridine-2-carboxylate

5-Amino-6-(5-amino-6-methoxy-quinolin-2-yl)-4-(2-benzyloxy-3,4-dimethoxy-phenyl)-3-methyl-pyridine-2-carboxylic acid methyl ester

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