Ethyl 4-(6-chloro-3-nitropyridin-2-yl)piperazine-1-carboxylate

Base Information

• Chemical Name: Ethyl 4-(6-chloro-3-nitropyridin-2-yl)piperazine-1-carboxylate
• CAS No.: 75167-21-4
• Molecular Formula: C12H15ClN4O4
• Molecular Weight: 314.728
• DSSTox Substance ID: DTXSID70517433
• Wikidata: Q82379439
• Mol file: 75167-21-4.mol

Synonyms:75167-21-4;Ethyl 4-(6-chloro-3-nitropyridin-2-yl)piperazine-1-carboxylate;SCHEMBL10964799;DTXSID70517433;AKMFLNXSGUYKJX-UHFFFAOYSA-N;6-chloro-2-(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine;4-(6-chloro-3-nitro-2-pyridinyl)-1-piperazinecarboxylic acid, ethyl ester;4-(6-chloro3-nitro-2-pyridinyl)-1-piperazinecarboxylic acid, ethyl ester

Chemical Property of Ethyl 4-(6-chloro-3-nitropyridin-2-yl)piperazine-1-carboxylate

Chemical Property:

• PSA: 91.49000
• LogP: 2.44780
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 314.0781827
• Heavy Atom Count: 21
• Complexity: 384

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1CCN(CC1)C2=C(C=CC(=N2)Cl)[N+](=O)[O-]

Technology Process of Ethyl 4-(6-chloro-3-nitropyridin-2-yl)piperazine-1-carboxylate

There total 1 articles about Ethyl 4-(6-chloro-3-nitropyridin-2-yl)piperazine-1-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: 91.3%

4-ethoxycarbonylpiperazine (120-43-4) → 2,6-dicholoro-3-nitropyridine (16013-85-7,136901-10-5) + 2-chloro-6-(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine (92741-37-2) + 4-(6-chloro-3-nitro-2-pyridinyl)-1-piperazinecarboxylic acid,ethyl ester (75167-21-4) + 2,6-bis(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine (92741-38-3)

Guidance literature:

With hydrogenchloride; triethylamine; In chloroform; at -5 - 0 ℃; for 2h;

DOI:10.1002/jhet.5570210309

Reference yield:

4-(6-chloro-3-nitro-2-pyridinyl)-1-piperazinecarboxylic acid,ethyl ester (75167-21-4) → enoxacine (74011-58-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 54.6 percent / 13percent ammonia / ethanol / 15 h / 100 - 110 °C / autoclave

2: 95 percent / acetic acid / 0.5 h / 90 °C

3: zinc powder, acetic acid / ethanol / 0.17 h / Heating

4: 42percent tetrafluoroboric acid, sodium nitrite / ethanol; H₂O / 0.17 h / -7 - -4 °C

5: 82.3 percent / toluene / 4 h / Heating

6: 10percent HCl / methanol / 2 h / Heating

7: ethanol / 2 h / Heating

8: 75.8 percent / Dowtherm A / 0.22 h / 248 - 249 °C

9: 1.) potassium carbonate / 1.) DMF, 100 deg C, 30 min; 2.) 100 deg C, 3 h

10: 72.9 percent / 15percent HCl / ethanol / 0.25 h / Heating

11: 87 percent / 10percent NaOH / ethanol / 4 h / Heating

With hydrogenchloride; ammonium hydroxide; sodium hydroxide; tetrafluoroboric acid; diphenyl ether-biphenyl eutectic; potassium carbonate; acetic acid; zinc; sodium nitrite; In methanol; ethanol; water; acetic acid; toluene;

DOI:10.1002/jhet.5570210309

Reference yield:

4-(6-chloro-3-nitro-2-pyridinyl)-1-piperazinecarboxylic acid,ethyl ester (75167-21-4) → 4-(6-Acetylamino-3-amino-pyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester (75167-24-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 54.6 percent / 13percent ammonia / ethanol / 15 h / 100 - 110 °C / autoclave

2: 95 percent / acetic acid / 0.5 h / 90 °C

3: zinc powder, acetic acid / ethanol / 0.17 h / Heating

With ammonium hydroxide; acetic acid; zinc; In ethanol; acetic acid;

DOI:10.1002/jhet.5570210309

upstream raw materials:

4-ethoxycarbonylpiperazine

Downstream raw materials:

enoxacine

6-amino-2-(4-ethoxycarbonyl-1-piperazinyl)-3-fluoropyridine

4-(6-Acetylamino-3-amino-pyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester

6-acetylamino-2-(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine

Refernces