2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile

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Chemical Name:2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile
CAS No.:711020-24-5
Molecular Formula:C₂₃H₁₆Cl₂N₂O₃
Molecular Weight:439.298
Hs Code.:

Synonyms:2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile

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Chemical Property of 2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile

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Technology Process of 2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile

There total 5 articles about 2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-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: 84.0%

: 711020-23-4
2-[(2S)-2-(3,4-dichlorophenyl)-4-hydroxybutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile

: 711020-24-5
2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 2.5h;
DOI:10.1016/j.bmc.2004.03.015

Reference yield:

: 263388-13-2
2-Methoxy-3-cyano-1-naphthoyl Chloride

: 711020-24-5
2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / aq. NaOH / CH₂Cl₂ / 0 - 20 °C

2: 89 percent / magnesium; iodine / benzene; diethyl ether / 1 h / Heating

3: sulfuric acid / CHCl₃ / 5 - 20 °C

4: 0.28 g / NaOH / tetrahydrofuran; H₂O; methanol / 2.75 h / 20 °C

5: 84 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 20 °C

With sodium hydroxide; oxalyl dichloride; sulfuric acid; iodine; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; benzene; 5: Swern oxidation;
DOI:10.1016/j.bmc.2004.03.015

Reference yield:

: acetic acid 4-(5-cyano-1-oxo-1H-naphtho[1,2-e][1,3]oxazin-2-yl)-3-(3,4-dichloro-phenyl)-butyl ester

: 711020-24-5
2-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-oxo-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine-5-carbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 0.28 g / NaOH / tetrahydrofuran; H₂O; methanol / 2.75 h / 20 °C

2: 84 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 20 °C

With sodium hydroxide; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 2: Swern oxidation;
DOI:10.1016/j.bmc.2004.03.015