N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide

Base Information

• Chemical Name: N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
• CAS No.: 350046-93-4
• Molecular Formula: C₁₇H₁₆N₂O₅
• Molecular Weight: 328.324
• DSSTox Substance ID: DTXSID101325878
• ChEMBL ID: CHEMBL2004075
• Mol file: 350046-93-4.mol

Synonyms:MLS000766675;CHEMBL2004075;DTXSID101325878;AKOS030517831;350046-93-4;N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide;SMR000414650;2,3-Dihydro-benzo[1,4]dioxine-2-carboxylic acid [1-(3-hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazide

Chemical Property of N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 328.10592162
• Heavy Atom Count: 24
• Complexity: 458

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=NNC(=O)C2COC3=CC=CC=C3O2)O
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=N\NC(=O)C2COC3=CC=CC=C3O2)O

Technology Process of N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide

There total 3 articles about N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,3-dihydro-1,4-benzodioxine-3-carboxamide 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: 81.0%

isovanillin (621-59-0) + 2,3-dihydro-1,4-benzodioxane-2-carbohydrazide (90557-92-9) → N'-[3-hydroxy-4-methoxyphenyl-methylidene]-2,3-dihydro-1,4-benzodioxine-2-carbohydrazide (350046-93-4)

Guidance literature:

With acetic acid; In ethanol; Reflux; Molecular sieve;

DOI:10.5012/bkcs.2012.33.2.575

Reference yield:

ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate (4739-94-0) → N'-[3-hydroxy-4-methoxyphenyl-methylidene]-2,3-dihydro-1,4-benzodioxine-2-carbohydrazide (350046-93-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / ethanol / 16 h / Reflux

2: acetic acid / ethanol / Reflux; Molecular sieve

With hydrazine hydrate; acetic acid; In ethanol;

DOI:10.5012/bkcs.2012.33.2.575

Reference yield:

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → N'-[3-hydroxy-4-methoxyphenyl-methylidene]-2,3-dihydro-1,4-benzodioxine-2-carbohydrazide (350046-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / 15 h / Reflux

2: hydrazine hydrate / ethanol / 16 h / Reflux

3: acetic acid / ethanol / Reflux; Molecular sieve

With potassium carbonate; hydrazine hydrate; acetic acid; In ethanol; acetone;

DOI:10.5012/bkcs.2012.33.2.575

upstream raw materials:

isovanillin

2,3-dihydro-1,4-benzodioxane-2-carbohydrazide

ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate

benzene-1,2-diol

Downstream raw materials:

N-(2-(3-hydroxy-4-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl)-2,3-dihydro-1,4-benzodioxine-2-carboxamide