N-(2-Amino-4-chlorophenyl)anthranilic acid

Base Information

• Chemical Name: N-(2-Amino-4-chlorophenyl)anthranilic acid
• CAS No.: 67990-66-3
• Molecular Formula: C13H11ClN2O2
• Molecular Weight: 262.696
• DSSTox Substance ID: DTXSID60346259
• Nikkaji Number: J236.481F
• Wikidata: Q82119194
• Mol file: 67990-66-3.mol

Synonyms:67990-66-3;N-(2-Amino-4-chlorophenyl)anthranilic acid;2-((2-Amino-4-chlorophenyl)amino)benzoic acid;2-(2-Amino-4-chloroanilino)benzoic acid;2-[(2-amino-4-chlorophenyl)amino]benzoic acid;Benzoic acid, 2-[(2-amino-4-chlorophenyl)amino]-;2-(2-amino-4-chlorophenylamino)benzoic acid;2-((2-Amino-4-chlorophenyl)amino)benzoicacid;BIDD:GT0706;SCHEMBL1365407;DTXSID60346259;MFCD00007775;AKOS005067379;N-(2-amino-4-chlorophenyl)anthranilic;AC-15013;BS-42303;2-(2-Amino-4-chloroanilino)benzoic acid #;FT-0641156;A835957;N-(2-Amino-4-chlorophenyl)anthranilic acid, 97%;2-[(2-azanyl-4-chloranyl-phenyl)amino]benzoic acid

Chemical Property of N-(2-Amino-4-chlorophenyl)anthranilic acid

Chemical Property:

• Vapor Pressure: 1.32E-08mmHg at 25°C
• Melting Point: 191 °C (dec.)(lit.)
• Refractive Index: 1.716
• Boiling Point: 442.4 °C at 760 mmHg
• PKA: 3.60±0.36(Predicted)
• Flash Point: 221.4 °C
• PSA: 75.35000
• Density: 1.441 g/cm³
• LogP: 4.01820
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 262.0509053
• Heavy Atom Count: 18
• Complexity: 301

Purity/Quality:

99% ^*data from raw suppliers

N-(2-Amino-4-chlorophenyl)anthranilic acid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)NC2=C(C=C(C=C2)Cl)N
• Uses: N-(2-Amino-4-chlorophenyl)anthranilic acid may be used in chemical synthesis studies.

Technology Process of N-(2-Amino-4-chlorophenyl)anthranilic acid

There total 15 articles about N-(2-Amino-4-chlorophenyl)anthranilic acid 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%

2-(4-Chlor-2-nitrophenyl)aminobenzencarbonsaeure (60091-87-4) → N-(2-Amino-4-chlorophenyl)anthranilic acid (67990-66-3)

Guidance literature:

With hydrogen; platinum on sulfide coal; In ethyl acetate; for 5h; under 1500.15 Torr;

Reference yield:

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → N-(2-Amino-4-chlorophenyl)anthranilic acid (67990-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / dimethylformamide / 140 °C

2: 90 percent / DVP-Fe, conc. HCl / aq. ethanol; H₂O / Heating

With hydrogenchloride; potassium carbonate; In ethanol; water; N,N-dimethyl-formamide;

Reference yield:

2-fluoro-5-chloronitrobenzene (345-18-6) → N-(2-Amino-4-chlorophenyl)anthranilic acid (67990-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 120 °C

2: iron; ammonium chloride / tetrahydrofuran; methanol; water / 2 h / 80 °C

With iron; ammonium chloride; caesium carbonate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2020.127563 DOI:10.1016/j.bmcl.2021.127911

upstream raw materials:

2-(4-Chlor-2-nitrophenyl)aminobenzencarbonsaeure

2-chloro-5-bromonitrobenzene

anthranilic acid

2,5-dichloronitrobenzene

Downstream raw materials:

8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

ethyl 4-(8-chloro-5H-dibenzo[b,e][1,4]diazepin-11-yl)benzoate

8,11-dichloro-5H-dibenzo[b,e][1,4]-diazepine

8-Chlor-5,10-dihydro-5--11H-dibenzo<1,4>-diazepin-11-on-hydrochlorid

Refernces

• 1、 -. "Clozapine intermediate as well as synthesis method and application thereof (by machine translation)". Paragraph 0022-0028; 0032-0035. . Retrieved 2020/10/14.
• 2、 -. "NOVEL and IMPROVED SYNTHESIS OF ANTIPSYCHOTIC DRUG". Page/Page column 17-18. . Retrieved 2020/01/08.