Methyl 6-bromo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

Base Information

• Chemical Name: Methyl 6-bromo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate
• CAS No.: 141761-85-5
• Molecular Formula: C10H8BrNO4
• Molecular Weight: 286.07900
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50576548
• Wikidata: Q82466303
• Mol file: 141761-85-5.mol

Synonyms:141761-85-5;Methyl 6-bromo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate;Methyl 6-bromo-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate;6-Bromo-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid methyl ester;methyl 6-bromo-3-oxo-4H-1,4-benzoxazine-8-carboxylate;MFCD12196467;Methyl 6-bromo-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate;C10H8BrNO4;FJLFERASKAOESO-UHFFFAOYSA-N;SCHEMBL4290919;DTXSID50576548;AKOS005073760;methyl 6-bromo-3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazine-8-carboxylate;ND-0042;SB33481;METHYL 6-BROMO-3,4-DIHYDRO-3-OXO-2H-1,4-BENZOXAZINE-8-CARBOXYLATE 95+%;CS-0313285;F83643;J-522535;Methyl6-bromo-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate;2H-1,4-Benzoxazine-8-carboxylic acid, 6-bromo-3,4-dihydro-3-oxo-, methyl ester

Chemical Property of Methyl 6-bromo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

Chemical Property:

• PSA: 64.63000
• LogP: 1.70460
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 284.96367
• Heavy Atom Count: 16
• Complexity: 309

Purity/Quality:

97% ^*data from raw suppliers

Methyl6-Bromo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C2C(=CC(=C1)Br)NC(=O)CO2

Technology Process of Methyl 6-bromo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

There total 4 articles about Methyl 6-bromo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-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:

5-Bromo-3-(2-chloro-acetylamino)-2-hydroxy-benzoic acid methyl ester → 6-Bromo-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid methyl ester (141761-85-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 2h; Yield given;

DOI:10.1248/cpb.40.624

Reference yield:

methyl 5-bromo-2-hydroxy-3-nitrobenzoate (91983-31-2) → 6-Bromo-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid methyl ester (141761-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91.3 percent / 0.78N aq. NH₄Cl, Fe / toluene / 1 h / 85 - 90 °C

2: aq. NaHCO₃ / CHCl₃ / 2 h / 0 - 10 °C

3: K₂CO₃ / dimethylformamide / 2 h / 70 °C

With iron; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; In chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.40.624

Reference yield:

5-bromo-2-hydroxy-benzoic acid methyl ester (4068-76-2) → 6-Bromo-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid methyl ester (141761-85-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 82.3 percent / HNO₃, conc. H₂SO₄ / 1 h / 0 - 5 °C

2: 91.3 percent / 0.78N aq. NH₄Cl, Fe / toluene / 1 h / 85 - 90 °C

3: aq. NaHCO₃ / CHCl₃ / 2 h / 0 - 10 °C

4: K₂CO₃ / dimethylformamide / 2 h / 70 °C

With sulfuric acid; nitric acid; iron; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; In chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.40.624

upstream raw materials:

methyl 5-bromo-2-hydroxy-3-nitrobenzoate

5-bromo-2-hydroxy-benzoic acid methyl ester

3-amino-5-bromo-2-hydroxybenzoic acid methyl ester

Downstream raw materials:

6-Bromo-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid methyl ester