Methyl 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate

Base Information

• Chemical Name: Methyl 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate
• CAS No.: 20197-76-6
• Molecular Formula: C10H11NO4
• Molecular Weight: 209.19900
• Hs Code.: 2932999099
• European Community (EC) Number: 814-601-8
• DSSTox Substance ID: DTXSID701201016
• Wikidata: Q107140084
• ChEMBL ID: CHEMBL1608835
• Mol file: 20197-76-6.mol

Synonyms:methyl 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate;20197-76-6;methyl 6-amino-2,3-dihydro-1,4-benzodioxine-7-carboxylate;methyl 7-amino-2,3-dihydro-1,4-benzodioxine-6-carboxylate;7-Amino-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester;7-AMINO-2,3-DIHYDRO-BENZO[1,4]DIOXINE-6-CARBOXYLICACID METHYL ESTER;BAS 03213168;MLS000709705;SCHEMBL666309;CHEMBL1608835;DTXSID701201016;HMS1684M20;HMS2686L21;MFCD03724048;AKOS000651226;SMR000286572;CS-0449305;EN300-2008337;A909017;SR-01000319033;6-amino-3,4-ethylenedioxybenzoic acid methyl ester;SR-01000319033-1;Methyl 7-amino-2,3-dihydro-1,4-benzodioxin-6-carboxylate;methyl7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate;7-Amino-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid, methyl ester;7-Amino-2,3-dihydro-benzo[1.4]dioxine-6-carboxylic acid methyl ester;7-amino-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid methyl ester

Chemical Property of Methyl 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate

Chemical Property:

• Boiling Point: 354.5±42.0 °C(Predicted)
• PKA: 2.71±0.20(Predicted)
• PSA: 70.78000
• Density: 1.319±0.06 g/cm3(Predicted)
• LogP: 1.40780
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 209.06880783
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

98%min ^*data from raw suppliers

Methyl7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1N)OCCO2

Technology Process of Methyl 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate

There total 5 articles about Methyl 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-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: 99.7%

7-nitro-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (52791-03-4) → 7-amino-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (20197-76-6)

Guidance literature:

With iron; acetic acid; In ethanol; water; Heating;

Reference yield:

2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (20197-75-5) → 7-amino-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (20197-76-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / HNO₃; glacial AcOH / 3 h / 70 °C

2: 90 percent / Fe; aq. NH₄Cl / methanol / 19 h / Heating

With nitric acid; iron; ammonium chloride; acetic acid; In methanol; 1: Nitration / 2: Reduction;

DOI:10.1021/jm000206a

Reference yield:

3,4-dihydroxybenzoic acid methyl ester (2150-43-8) → 7-amino-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester (20197-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide; ethanol

2: acetic acid; nitric acid

3: Raney nickel; acetic acid / Hydrogenation

With potassium hydroxide; ethanol; nitric acid; nickel; acetic acid;

upstream raw materials:

7-nitro-2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

3,4-dihydroxybenzoic acid methyl ester

2,3-dihydro-1,4-benzodioxin-6-carboxylic acid

Downstream raw materials:

7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid

3,4,7,8-tetrahydro[1,4]dioxino[2,3-g]quinazolin-4-one

Refernces

• 1、 -. "As the PI3K/mTOR inhibitor tricyclic compound, its preparation and use". Paragraph 0176; 0179. . Retrieved 2017/08/25.
• 2、 -. "SUBSTITUTED 3-CYANOQUINOLINES AS PROTEIN TYROSINE KINASES INHIBITORS". Page 72. . Retrieved 2010/02/04.