(2S)-8-Amino-2-methyl-2H-1,4-benzoxazin-3(4H)-one

Base Information

• Chemical Name: (2S)-8-Amino-2-methyl-2H-1,4-benzoxazin-3(4H)-one
• CAS No.: 870065-11-5
• Molecular Formula: C₉H₁₀N₂O₂
• Molecular Weight: 178.191
• DSSTox Substance ID: DTXSID001232585
• Mol file: 870065-11-5.mol

Synonyms:(2S)-8-Amino-2-methyl-2H-1,4-benzoxazin-3(4H)-one;DTXSID001232585;870065-11-5

Chemical Property of (2S)-8-Amino-2-methyl-2H-1,4-benzoxazin-3(4H)-one

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 178.074227566
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(=O)NC2=CC=CC(=C2O1)N
• Isomeric SMILES: C[C@H]1C(=O)NC2=CC=CC(=C2O1)N

Technology Process of (2S)-8-Amino-2-methyl-2H-1,4-benzoxazin-3(4H)-one

There total 2 articles about (2S)-8-Amino-2-methyl-2H-1,4-benzoxazin-3(4H)-one 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:

6-chloro-(S)-2-methyl-8-nitro-4H-benzo[1,4]oxazin-3-one (870065-07-9) → (S)-2-methyl-8-amino-4H-benzo[1,4]oxazin-3-one (870065-11-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; for 24h;

DOI:10.1021/jm050148z

Reference yield:

4-chloro-6-nitro-2-aminophenol (6358-08-3) → (S)-2-methyl-8-amino-4H-benzo[1,4]oxazin-3-one (870065-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Ph₃P; DIAD / tetrahydrofuran / 96 h / 20 °C

2: H₂ / Pd/C / ethanol; ethyl acetate / 24 h

With di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; ethyl acetate; 1: Mitsunobu reaction;

DOI:10.1021/jm050148z

Reference yield:

(S)-2-methyl-8-amino-4H-benzo[1,4]oxazin-3-one (870065-11-5) → 8-{4-[3-(5-fluoro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-2-methyl-4H-benzo[1,4]oxazin-3-one

Guidance literature:

Multi-step reaction with 2 steps

1: chlorobenzene / 69 h / Heating

2: KI; DIPEA / acetonitrile / 18 h / Heating

With N-ethyl-N,N-diisopropylamine; potassium iodide; In chlorobenzene; acetonitrile;

DOI:10.1021/jm050148z

upstream raw materials:

6-chloro-(S)-2-methyl-8-nitro-4H-benzo[1,4]oxazin-3-one

4-chloro-6-nitro-2-aminophenol