11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile

Base Information

• Chemical Name: 11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile
• CAS No.: 367261-21-0
• Molecular Formula: C₂₆H₂₂Cl₂N₂O₃
• Molecular Weight: 481.378
• Mol file: 367261-21-0.mol

Synonyms:11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile

Chemical Property of 11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile

There total 9 articles about 11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile 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: 47.0%

(4R)-2-[(2S)-2-(3,4-dichlorophenyl)pent-4-en-1-yl]-4-methyl-1-oxo-1,3,4,6-tetrahydro-2H-naphtho[1,2-f][1,4]oxazocine-7-carbonitrile (367261-19-6) → 11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile (367261-21-0)

Guidance literature:

(4R)-2-[(2S)-2-(3,4-dichlorophenyl)pent-4-en-1-yl]-4-methyl-1-oxo-1,3,4,6-tetrahydro-2H-naphtho[1,2-f][1,4]oxazocine-7-carbonitrile; With ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane; at -30 - 20 ℃;

DOI:10.1016/j.bmc.2004.03.015

Reference yield:

(2S)-2-(3,4-dichlorophenyl)pent-4-enoic acid (147643-57-0) → 11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile (367261-21-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 98 percent / N,N-diisopropylethylamine; 4-dimethylaminopyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Heating

2.1: lithium aluminum hydride / diethyl ether; tetrahydrofuran / Heating

3.1: sodium carbonate / dioxane; H₂O

4.1: 77 percent / sodium hydride / dimethylformamide; tetrahydrofuran / 50 - 60 °C

5.1: trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

6.1: 88 percent / pyridine hydrochloride / 180 °C

7.1: 58 percent / N,N-diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / acetonitrile

8.1: ozone / CH₂Cl₂; methanol / -78 °C

8.2: 47 percent / dimethyl sulfide / CH₂Cl₂; methanol / -30 - 20 °C

With dmap; lithium aluminium tetrahydride; pyridine hydrochloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; sodium carbonate; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2004.03.015

Reference yield:

methyl 3-cyano-2-methyl-1-naphthoate (263862-16-4) → 11-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-9-methyl-12-oxo-9,10,11,12-tetrahydro-7H-8-oxa-11-aza-cycloocta[a]naphthalene-6-carbonitrile (367261-21-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-bromosuccinimide; 2,2'-azobis(2-methylisobutyronitrile) / CCl₄ / 3 h / Heating

2.1: 77 percent / sodium hydride / dimethylformamide; tetrahydrofuran / 50 - 60 °C

3.1: trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

4.1: 88 percent / pyridine hydrochloride / 180 °C

5.1: 58 percent / N,N-diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / acetonitrile

6.1: ozone / CH₂Cl₂; methanol / -78 °C

6.2: 47 percent / dimethyl sulfide / CH₂Cl₂; methanol / -30 - 20 °C

With N-Bromosuccinimide; 2,2'-azobis(2-methylisobutyronitrile); pyridine hydrochloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2004.03.015

upstream raw materials:

(4R)-2-[(2S)-2-(3,4-dichlorophenyl)pent-4-en-1-yl]-4-methyl-1-oxo-1,3,4,6-tetrahydro-2H-naphtho[1,2-f][1,4]oxazocine-7-carbonitrile

(2S)-2-(3,4-dichlorophenyl)pent-4-enoic acid

methyl 3-cyano-2-methyl-1-naphthoate

methyl 2-(bromomethyl)-3-cyano-1-naphthoate

Downstream raw materials:

(S)-4-((R)-6-Cyano-9-methyl-12-oxo-7,9,10,12-tetrahydro-8-oxa-11-aza-cycloocta[a]naphthalen-11-yl)-3-(3,4-dichloro-phenyl)-butyryl chloride