2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene

Base Information

• Chemical Name: 2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene
• CAS No.: 130627-31-5
• Molecular Formula: C₂₁H₁₇NO₆
• Molecular Weight: 379.369
• Mol file: 130627-31-5.mol

Synonyms:2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene

Chemical Property of 2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene

There total 19 articles about 2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene 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: 70.0%

N-[6-(2,3-Dihydroxy-7-methoxy-2-methyl-2,3-dihydro-benzofuran-4-yl)-naphtho[2,3-d][1,3]dioxol-5-yl]-N-methyl-formamide (145654-08-6) → 2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene (130627-31-5)

Guidance literature:

With periodic acid; In 1,4-dioxane; water; for 2h; Ambient temperature;

DOI:10.1248/cpb.40.2002

Reference yield:

2-<4-(7-methoxy-2-methyl-2H-benzofuranyl)>-1-(N-methylformamido)-6,7-methylenedioxynaphthalene (130627-27-9) → 2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene (130627-31-5)

Guidance literature:

Multistep reaction;

DOI:10.1248/cpb.38.1775

Reference yield:

isovanillin (621-59-0) → 2-(2-formyl-3-hydroxy-4-methoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene (130627-31-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / K₂CO₃ / dimethylformamide / 4 h / Ambient temperature

2: 22 percent / CsF, N,N-diethylaniline / 2 h / Heating

3: 94 percent / 10percent NaOH / ethanol / Ambient temperature

4: 87 percent / acetic acid / 2-ethoxy-ethanol; H₂O / 0.08 h / 110 - 120 °C

5: 91 percent / NaOH / H₂O; ethanol / 4 h / Heating

6: 94 percent / H₂, 1percent aq.PdCl₂, Norit / acetic acid / 760 Torr / Ambient temperature

7: 86 percent / POCl₃, K₂CO₃ / acetonitrile / 2.5 h / 55 - 60 °C

8: 1.) TiCl₄, 2.) NaBH₄ / 1.) CHCl₃, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight

9: 91 percent / CHCl₃ / 3 h / Heating

10: 89 percent / DDQ / benzene / 2 h / Heating

11: 77 percent / OsO₄, pyridine / 2 h / Ambient temperature

12: 70 percent / HIO₄*2H₂O / H₂O; dioxane / 2 h / Ambient temperature

With pyridine; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; hydrogen; titanium tetrachloride; potassium carbonate; pyrographite; acetic acid; periodic acid; cesium fluoride; N,N-diethylaniline; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; trichlorophosphate; In 1,4-dioxane; 2-ethoxy-ethanol; ethanol; chloroform; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1248/cpb.40.2002

upstream raw materials:

2-<4-(7-methoxy-2-methyl-2H-benzofuranyl)>-1-(N-methylformamido)-6,7-methylenedioxynaphthalene

N-[6-(2,3-Dihydroxy-7-methoxy-2-methyl-2,3-dihydro-benzofuran-4-yl)-naphtho[2,3-d][1,3]dioxol-5-yl]-N-methyl-formamide

isovanillin

1-(benzo[d][1,3]dioxol-6-yl)ethanone

Downstream raw materials:

chelerythrine chloride

2-(2-formyl-3,4-dimethoxyphenyl)-1-(N-methylformamido)-6,7-methylenedioxynaphthalene

chelerythrine

Refernces

• 1、 Ishii,Ishikawa,Takeda,Suzuki,Harayaya. "Total synthesis of chelerythrine, a benzo[c]phenanthridine alkaloid". . p. 2002 - 2006. Retrieved 2007/10/02.