5-Methyl-5H-dibenz[b,d]azepine-6,7-dione 7-Oxime

Base Information

• Chemical Name: 5-Methyl-5H-dibenz[b,d]azepine-6,7-dione 7-Oxime
• CAS No.: 209984-31-6
• Molecular Formula: C₁₅H₁₂N₂O₂
• Molecular Weight: 252.272
• Hs Code.: 2933990090
• Mol file: 209984-31-6.mol

Synonyms:5-Methyl-5H-dibenz[b,d]azepine-6,7-dione 7-Oxime;5H-Dibenz[b,d]azepine-6,7-dione, 5-Methyl-, 7-oxiMe;(E)-7-(Hydroxyimino)-5-methyl-5H-dibenzo[b,d]azepin-6(7H)-one

Chemical Property of 5-Methyl-5H-dibenz[b,d]azepine-6,7-dione 7-Oxime

Chemical Property:

• PSA: 54.59000
• LogP: 1.98160
• Storage Temp.: 2-8°C
• Solubility.: Ethanol, Methanol

Purity/Quality:

≥95% ^*data from raw suppliers

5-Methyl-5H-dibenz[b,d]azepine-6,7-dione 7-oxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: An intermediate in the preparation of γ-secretase inhibitors

Technology Process of 5-Methyl-5H-dibenz[b,d]azepine-6,7-dione 7-Oxime

There total 10 articles about 5-Methyl-5H-dibenz[b,d]azepine-6,7-dione 7-Oxime 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: 100.0%

N-methyl-5H-dibenzo[b,d]azepin-6(7H)-one (209984-30-5) → 7-methyl-5-oximo-5,7-dihydro-6H-dibenz[b,d]azepin-6-one (209984-31-6)

Guidance literature:

With n-Butyl nitrite; potassium hexamethylsilazane; In toluene;

DOI:10.1016/j.bmcl.2007.07.062

Reference yield:

2-(2-iodophenyl)acetonitrile (40400-15-5) → 7-methyl-5-oximo-5,7-dihydro-6H-dibenz[b,d]azepin-6-one (209984-31-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pinacolborane; Et₃N; 2-(dicyclohexylphosphino)biphenyl / Pd(OAc)2 / dioxane / 80 °C

1.2: 100 percent / aq. Ba(OH)2*8H₂O / dioxane / 100 °C

2.1: NaNO₂; aq. HCl / tetrahydrofuran / 0 °C

2.2: NaN₃ / tetrahydrofuran / 0 - 20 °C

3.1: DIBALH / CH₂Cl₂ / -78 °C

4.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 0 - 20 °C

5.1: 100 percent / DCC / CH₂Cl₂ / 20 °C

6.1: 76 percent / n-Bu₃P / toluene / 20 °C

7.1: NaH / dimethylformamide / 0 - 20 °C

8.1: n-BuONO; KHMDS / tetrahydrofuran / 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pinacol borane; n-Butyl nitrite; tributylphosphine; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; CyJohnPhos; sodium nitrite; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.2: Suzuki-Miyaura coupling / 6.1: Staudinger-aza-Wittig reaction;

DOI:10.1016/j.tetlet.2004.01.087

Reference yield:

2-bromoaniline (615-36-1) → 7-methyl-5-oximo-5,7-dihydro-6H-dibenz[b,d]azepin-6-one (209984-31-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pinacolborane; Et₃N; 2-(dicyclohexylphosphino)biphenyl / Pd(OAc)2 / dioxane / 80 °C

1.2: 100 percent / aq. Ba(OH)2*8H₂O / dioxane / 100 °C

2.1: NaNO₂; aq. HCl / tetrahydrofuran / 0 °C

2.2: NaN₃ / tetrahydrofuran / 0 - 20 °C

3.1: DIBALH / CH₂Cl₂ / -78 °C

4.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 0 - 20 °C

5.1: 100 percent / DCC / CH₂Cl₂ / 20 °C

6.1: 76 percent / n-Bu₃P / toluene / 20 °C

7.1: NaH / dimethylformamide / 0 - 20 °C

8.1: n-BuONO; KHMDS / tetrahydrofuran / 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pinacol borane; n-Butyl nitrite; tributylphosphine; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; CyJohnPhos; sodium nitrite; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.2: Suzuki-Miyaura coupling / 6.1: Staudinger-aza-Wittig reaction;

DOI:10.1016/j.tetlet.2004.01.087

upstream raw materials:

N-methyl-5H-dibenzo[b,d]azepin-6(7H)-one

5H,7H-dibenzo[b,d]azepin-6-one

2-(2-iodophenyl)acetonitrile

2-bromoaniline

Downstream raw materials:

7-amino-5-methyl-5H-dibenzo[b,d]azepin-6(7H)-one hydrochloride

7-(L-alaninyl)-amino-5-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one

Refernces

• 1、 Fauq, Abdul H.,Simpson, Katherine,Maharvi, Ghulam M.,Golde, Todd,Das, Pritam. "A multigram chemical synthesis of the γ-secretase inhibitor LY411575 and its diastereoisomers". . p. 6392 - 6395. Retrieved 2008/09/16.
• 2、 Fuwa, Haruhiko,Okamura, Yumiko,Morohashi, Yuichi,Tomita, Taisuke,Iwatsubo, Takeshi,Kan, Toshiyuki,Fukuyama, Tohru,Natsugari, Hideaki. "Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues". . p. 2323 - 2326. Retrieved 2007/10/03.