3,4-Dihydro-7-methoxy-2-methylene-3-oxo-2H-1,4-benzoxazine-5-carboxylic acid

Base Information

• Chemical Name: 3,4-Dihydro-7-methoxy-2-methylene-3-oxo-2H-1,4-benzoxazine-5-carboxylic acid
• CAS No.: 105897-30-1
• Molecular Formula: C₁₁H₉NO₅
• Molecular Weight: 235.196
• DSSTox Substance ID: DTXSID10147410
• Metabolomics Workbench ID: 70491
• Nikkaji Number: J387.985B
• Wikidata: Q27105448
• Mol file: 105897-30-1.mol

Synonyms:3,4-dihydro-7-methoxy-2-methylene-3-oxo-2H-1,4-benzoxazine-5-carboxylic acid;degradation product II-F3

Chemical Property of 3,4-Dihydro-7-methoxy-2-methylene-3-oxo-2H-1,4-benzoxazine-5-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.9E-11mmHg at 25°C
• Boiling Point: 507.8°Cat760mmHg
• Flash Point: 260.9°C
• PSA: 92.53000
• Density: 1.47g/cm³
• LogP: 0.51930
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 235.04807239
• Heavy Atom Count: 17
• Complexity: 367

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C2C(=C1)OC(=C)C(=O)N2)C(=O)O

Technology Process of 3,4-Dihydro-7-methoxy-2-methylene-3-oxo-2H-1,4-benzoxazine-5-carboxylic acid

There total 8 articles about 3,4-Dihydro-7-methoxy-2-methylene-3-oxo-2H-1,4-benzoxazine-5-carboxylic acid 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: 36.0%

methyl 7-methoxy-2-methylene-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-carboxylate (85691-10-7) → 7-methoxy-2-methylene-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-carboxylic acid (105897-30-1)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; for 1.5h;

DOI:10.1039/c4cc07003h

Reference yield:

2-Nitro-3,5-dimethoxybenzoate de methyle (76746-30-0) → 7-methoxy-2-methylene-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-carboxylic acid (105897-30-1)

Guidance literature:

Multi-step reaction with 7 steps

1: aluminum (III) chloride / dichloromethane / 2.5 h / 0 - 20 °C

2: potassium carbonate / dichloromethane; methanol / 3 h / Reflux

3: hydrogenchloride; tin(II) chloride dihdyrate / ethanol; water / 4 h / Reflux

4: pyridine / dichloromethane / 0.25 h / 0 - 20 °C

5: Pd(OH)2/C; cyclohexa-1,4-diene / ethanol / 0.08 h / 50 °C

6: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / 0 °C

7: lithium hydroxide monohydrate / methanol; water; tetrahydrofuran / 1.5 h

With pyridine; hydrogenchloride; aluminum (III) chloride; tin(II) chloride dihdyrate; lithium hydroxide monohydrate; cyclohexa-1,4-diene; Pd(OH)2/C; potassium carbonate; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1039/c4cc07003h

Reference yield:

methyl 3-hydroxy-5-methoxy-2-nitrobenzoate (105897-21-0) → 7-methoxy-2-methylene-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-carboxylic acid (105897-30-1)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate / dichloromethane; methanol / 3 h / Reflux

2: hydrogenchloride; tin(II) chloride dihdyrate / ethanol; water / 4 h / Reflux

3: pyridine / dichloromethane / 0.25 h / 0 - 20 °C

4: Pd(OH)2/C; cyclohexa-1,4-diene / ethanol / 0.08 h / 50 °C

5: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / dichloromethane / 1.5 h / 0 °C

6: lithium hydroxide monohydrate / methanol; water; tetrahydrofuran / 1.5 h

With pyridine; hydrogenchloride; tin(II) chloride dihdyrate; lithium hydroxide monohydrate; cyclohexa-1,4-diene; Pd(OH)2/C; potassium carbonate; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1039/c4cc07003h

upstream raw materials:

2-Nitro-3,5-dimethoxybenzoate de methyle

methyl 3-hydroxy-5-methoxy-2-nitrobenzoate

methyl 3-(benzyloxy)-5-methoxy-2-nitrobenzoate

methyl 3,5-dimethoxybenzoate