5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline

Base Information

• Chemical Name: 5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline
• CAS No.: 690254-87-6
• Molecular Formula: C₂₂H₂₂N₂O₄
• Molecular Weight: 378.428
• Mol file: 690254-87-6.mol

Synonyms:5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline

Chemical Property of 5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline

There total 9 articles about 5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline 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: 45.0%

pyruvoyl chloride (5704-66-5) + 1-azidomethyl-5-benzyloxy-7-methoxy-6-methylisoquinoline (690254-86-5) → 5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline (690254-87-6)

Guidance literature:

1-azidomethyl-5-benzyloxy-7-methoxy-6-methylisoquinoline; With triphenylphosphine; In benzene; at 20 ℃; for 12h;

pyruvoyl chloride; In benzene; at 20 ℃; for 0.0833333h; Further stages.;

DOI:10.1016/j.tet.2004.02.010

Reference yield:

2-hydroxy-4-methoxy-3-methylbenzaldehyde (54700-36-6) → 5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline (690254-87-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 99 percent / K₂CO₃ / dimethylformamide / 4 h / 60 °C

2.1: 88 percent / mCPBA / CH₂Cl₂ / 1 h / 60 °C

3.1: 53 percent / AcOH / 3 h / 110 °C

4.1: 81 percent / pyridine / CH₂Cl₂ / 1 h / cooling

5.1: 90 percent / Et₄NCl; PdCl₂(PPh₃)2 / dimethylformamide / 1.5 h / 110 °C

6.1: Mg; 1,2-dibromoethane / tetrahydrofuran

6.2: tetrahydrofuran / 2 h / 20 °C

6.3: 87 percent / H₂O₂; KHCO₃; KF / tetrahydrofuran; methanol / 3 h / 20 °C

7.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

8.1: 85 percent / pyridinium chlorochromate; celite / CH₂Cl₂ / 10 h / 20 °C

9.1: 57 percent / NH₂OH*HCl; AcONa / ethanol / 1 h / 85 °C

10.1: 49 percent / various solvent(s) / 1 h / 180 °C

11.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

12.1: PhLi / cyclohexane; diethyl ether; dioxane / 0.17 h / cooling

12.2: 64 percent / cyclohexane; diethyl ether; dioxane / 0.5 h / 20 °C

13.1: 81 percent / NaN₃ / H₂O; dioxane / 1 h / 60 °C

14.1: PPh₃ / benzene / 12 h / 20 °C

14.2: 45 percent / benzene / 0.08 h / 20 °C

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; sodium azide; Celite; hydroxylamine hydrochloride; tetraethylammonium chloride; tetrabutyl ammonium fluoride; sodium acetate; potassium carbonate; magnesium; acetic acid; phenyllithium; ethylene dibromide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; benzene; 2.1: Baeyer-Villiger reaction / 3.1: Duff reaction / 6.2: Grignard reaction;

DOI:10.1016/j.tet.2004.02.010

Reference yield:

2-(benzyloxy)-4-methoxy-3-methylphenol (105103-95-5) → 5-benzyloxy-7-methoxy-6-methyl-1-(pyruvoylaminomethyl)isoquinoline (690254-87-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 53 percent / AcOH / 3 h / 110 °C

2.1: 81 percent / pyridine / CH₂Cl₂ / 1 h / cooling

3.1: 90 percent / Et₄NCl; PdCl₂(PPh₃)2 / dimethylformamide / 1.5 h / 110 °C

4.1: Mg; 1,2-dibromoethane / tetrahydrofuran

4.2: tetrahydrofuran / 2 h / 20 °C

4.3: 87 percent / H₂O₂; KHCO₃; KF / tetrahydrofuran; methanol / 3 h / 20 °C

5.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

6.1: 85 percent / pyridinium chlorochromate; celite / CH₂Cl₂ / 10 h / 20 °C

7.1: 57 percent / NH₂OH*HCl; AcONa / ethanol / 1 h / 85 °C

8.1: 49 percent / various solvent(s) / 1 h / 180 °C

9.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

10.1: PhLi / cyclohexane; diethyl ether; dioxane / 0.17 h / cooling

10.2: 64 percent / cyclohexane; diethyl ether; dioxane / 0.5 h / 20 °C

11.1: 81 percent / NaN₃ / H₂O; dioxane / 1 h / 60 °C

12.1: PPh₃ / benzene / 12 h / 20 °C

12.2: 45 percent / benzene / 0.08 h / 20 °C

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; sodium azide; Celite; hydroxylamine hydrochloride; tetraethylammonium chloride; tetrabutyl ammonium fluoride; sodium acetate; magnesium; acetic acid; phenyllithium; ethylene dibromide; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; benzene; 1.1: Duff reaction / 4.2: Grignard reaction;

DOI:10.1016/j.tet.2004.02.010

upstream raw materials:

pyruvoyl chloride

1-azidomethyl-5-benzyloxy-7-methoxy-6-methylisoquinoline

2-hydroxy-4-methoxy-3-methylbenzaldehyde

2-(benzyloxy)-4-methoxy-3-methylphenol

Refernces