Methyl (3Z)-6-chloro-2-hydroxy-3-(phenylmethoxycarbonylhydrazinylidene)-1H-indene-2-carboxylate

Base Information

• Chemical Name: Methyl (3Z)-6-chloro-2-hydroxy-3-(phenylmethoxycarbonylhydrazinylidene)-1H-indene-2-carboxylate
• CAS No.: 173903-19-0
• Molecular Formula: C19H17ClN2O5
• Molecular Weight: 388.8017
• DSSTox Substance ID: DTXSID801103142
• Mol file: 173903-19-0.mol

Synonyms:173903-19-0;Methyl (3Z)-6-chloro-2-hydroxy-3-(phenylmethoxycarbonylhydrazinylidene)-1H-indene-2-carboxylate;Hydrazinecarboxylic acid, (5-chloro-2,3-dihydro-2-hydroxy-2-(methoxyca rbonyl)-1H-inden-1-ylidene)-,;SCHEMBL8474618;SCHEMBL23224053;DTXSID801103142;Hydrazinecarboxylic acid, (5-chloro-2,3-dihydro-2-hydroxy-2-(methoxycarbonyl)-1H-inden-1-ylidene)-, phenylmethyl ester, (Z)-(+)-;Hydrazinecarboxylic acid, [5-chloro-2,3-dihydro-2-hydroxy-2-(methoxycarbonyl)-1H-inden-1-ylidene]-, phenylmethyl ester, (Z)-(+)-

Chemical Property of Methyl (3Z)-6-chloro-2-hydroxy-3-(phenylmethoxycarbonylhydrazinylidene)-1H-indene-2-carboxylate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 100.71000
• Density: 1.38g/cm³
• LogP: 2.63510
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 388.0825993
• Heavy Atom Count: 27
• Complexity: 593

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CC2=C(C1=NNC(=O)OCC3=CC=CC=C3)C=CC(=C2)Cl)O
• Isomeric SMILES: COC(=O)C\1(CC2=C(/C1=N/NC(=O)OCC3=CC=CC=C3)C=CC(=C2)Cl)O

Technology Process of Methyl (3Z)-6-chloro-2-hydroxy-3-(phenylmethoxycarbonylhydrazinylidene)-1H-indene-2-carboxylate

There total 4 articles about Methyl (3Z)-6-chloro-2-hydroxy-3-(phenylmethoxycarbonylhydrazinylidene)-1H-indene-2-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: 90.0%

N-benzyloxycarbonyl-hydrazine (5331-43-1) + (S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester → (S)-benzyl 2-(5-chloro-2-hydroxy-2-(methoxycarbonyl)-2,3-dihydro-1H-inden-1-ylidene)-hydrazine-1-carboxylate (173903-19-0)

Guidance literature:

With toluene-4-sulfonic acid; In chloroform; for 5h; Inert atmosphere; Reflux;

DOI:10.1002/adsc.201801263

Reference yield: 85.0%

N-benzyloxycarbonyl-hydrazine (5331-43-1) + (R)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester → (S)-benzyl 2-(5-chloro-2-hydroxy-2-(methoxycarbonyl)-2,3-dihydro-1H-inden-1-ylidene)-hydrazine-1-carboxylate (173903-19-0)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1002/adsc.201500911

Reference yield:

methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate (65738-56-9) → (S)-benzyl 2-(5-chloro-2-hydroxy-2-(methoxycarbonyl)-2,3-dihydro-1H-inden-1-ylidene)-hydrazine-1-carboxylate (173903-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2'-bromo-6`-hydroxy dihydroquinine; dihydrogen peroxide / water; dichloromethane / 48 h / 5 °C

2: toluene-4-sulfonic acid / methanol / 4 h / 80 °C / Inert atmosphere

With 2'-bromo-6`-hydroxy dihydroquinine; dihydrogen peroxide; toluene-4-sulfonic acid; In methanol; dichloromethane; water;

DOI:10.1002/adsc.201500911

upstream raw materials:

N-benzyloxycarbonyl-hydrazine

methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

(R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester