Methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate

Base Information

• Chemical Name: Methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate
• CAS No.: 214476-00-3
• Molecular Formula: C₁₄H₂₀N₂O₄
• Molecular Weight: 280.324
• DSSTox Substance ID: DTXSID101156821
• Mol file: 214476-00-3.mol

Synonyms:SCHEMBL6381760;STIXSFPLHFQZNA-UHFFFAOYSA-N;DTXSID101156821;methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate;Methyl 2-[[(dimethylamino)methylene]amino]-4-ethoxy-5-methoxybenzoate;214476-00-3

Chemical Property of Methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 280.14230712
• Heavy Atom Count: 20
• Complexity: 333

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC1=C(C=C(C(=C1)N=CN(C)C)C(=O)OC)OC

Technology Process of Methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate

There total 4 articles about Methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate 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:

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 2-amino-4-ethoxy-5-methoxybenzoic acid methyl ester (50413-49-5) → methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate (214476-00-3)

Guidance literature:

at 100 ℃; for 9.5h;

Reference yield:

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate (214476-00-3)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 100 °C

2: nitric acid; acetic acid / 2 h / 50 °C

3: iron; ammonium chloride / methanol; water / 15 h / Heating / reflux

4: 9.5 h / 100 °C

With nitric acid; iron; potassium carbonate; ammonium chloride; acetic acid; In methanol; water; N,N-dimethyl-formamide;

Reference yield:

4-ethoxy-3-methoxybenzoic acid methyl ester (3535-24-8) → methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate (214476-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1: nitric acid; acetic acid / 2 h / 50 °C

2: iron; ammonium chloride / methanol; water / 15 h / Heating / reflux

3: 9.5 h / 100 °C

With nitric acid; iron; ammonium chloride; acetic acid; In methanol; water;

upstream raw materials:

N,N-dimethyl-formamide dimethyl acetal

2-amino-4-ethoxy-5-methoxybenzoic acid methyl ester

4-hydroxy-3-methoxybenzoic acid methyl ester

4-ethoxy-3-methoxybenzoic acid methyl ester

Downstream raw materials:

7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-quinoline-3-carbonitrile

4-chloro-7-ethoxy-6-methoxy-quinoline-3-carbonitrile