β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate

Base Information

• Chemical Name: β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate
• CAS No.: 145220-92-4
• Molecular Formula: C₁₉H₁₇N₃O₇
• Molecular Weight: 399.36

Synonyms:β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate

Chemical Property of β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate

There total 11 articles about β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate 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: 68.6%

β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate (145220-91-3) → β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate (145220-92-4)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1248/cpb.40.1799

Reference yield:

4,4-dimethoxy-3-oxo-butyric acid methyl ester (60705-25-1) → β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate (145220-92-4)

Guidance literature:

Multi-step reaction with 10 steps

1: morpholine, AcOH

2: 100 percent / 3 h / 70 - 120 °C

3: 67 percent / 6 N HCl / acetone / 6 h / Ambient temperature

4: NH₂OH*HCl, NaOAc / acetic acid / 1 h / Ambient temperature

5: Ac₂O / acetic acid / 1.) RT, 1 h, 2.) 97-105 deg C, 4.5 h

6: 87.1 percent / 98percent HCO₂H / 5 h / Ambient temperature

7: PCl₅ / CHCl₃ / 1.5 h

8: pyridine / CHCl₃ / 2.5 h

9: 88.5 percent / p-TsOH*H₂O / methanol / 4 h / Ambient temperature

10: 68.6 percent / MnO₂ / CH₂Cl₂ / 8 h / Ambient temperature

With morpholine; pyridine; hydrogenchloride; manganese(IV) oxide; formic acid; phosphorus pentachloride; hydroxylamine hydrochloride; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; chloroform; acetic acid; acetone;

DOI:10.1248/cpb.40.1799

Reference yield:

3-nitro-benzaldehyde (99-61-6) → β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)pyridine-5-carboxylate (145220-92-4)

Guidance literature:

Multi-step reaction with 10 steps

1: morpholine, AcOH

2: 100 percent / 3 h / 70 - 120 °C

3: 67 percent / 6 N HCl / acetone / 6 h / Ambient temperature

4: NH₂OH*HCl, NaOAc / acetic acid / 1 h / Ambient temperature

5: Ac₂O / acetic acid / 1.) RT, 1 h, 2.) 97-105 deg C, 4.5 h

6: 87.1 percent / 98percent HCO₂H / 5 h / Ambient temperature

7: PCl₅ / CHCl₃ / 1.5 h

8: pyridine / CHCl₃ / 2.5 h

9: 88.5 percent / p-TsOH*H₂O / methanol / 4 h / Ambient temperature

10: 68.6 percent / MnO₂ / CH₂Cl₂ / 8 h / Ambient temperature

With morpholine; pyridine; hydrogenchloride; manganese(IV) oxide; formic acid; phosphorus pentachloride; hydroxylamine hydrochloride; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; chloroform; acetic acid; acetone;

DOI:10.1248/cpb.40.1799

upstream raw materials:

β-hydroxyisopropyl 2-cyano-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate

4,4-dimethoxy-3-oxo-butyric acid methyl ester

3-nitro-benzaldehyde

(E,Z)-methyl 4,4-dimethoxy-2-(3-nitrobenzylidene)acetoacetate

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