tert-Butyl (3-nitropyridin-4-yl)carbamate

Base Information

• Chemical Name: tert-Butyl (3-nitropyridin-4-yl)carbamate
• CAS No.: 623562-22-1
• Molecular Formula: C₁₀H₁₃N₃O₄
• Molecular Weight: 239.231
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID80446503
• Nikkaji Number: J1.950.759I
• Wikidata: Q82265162
• Mol file: 623562-22-1.mol

Synonyms:623562-22-1;tert-Butyl (3-nitropyridin-4-yl)carbamate;4-(N-Boc-amino)-3-nitropyridine;Tert-butyl N-(3-nitropyridin-4-yl)carbamate;tert-Butyl(3-nitropyridin-4-yl)carbamate;SCHEMBL15953139;DTXSID80446503;OBEIOYAIAXCJDI-UHFFFAOYSA-N;YZA56222;MFCD11520507;SB37976;CS-0272786;EN300-6989578;(3-Nitro-4-pyridyl)carbamic acid tert-butyl ester;A868496;Tert-butyl (3-nitropyridin-4(1h)-ylidene)carbamate;(3-nitro-pyridin-4-yl)-carbamic acid tert-butyl ester

Chemical Property of tert-Butyl (3-nitropyridin-4-yl)carbamate

Chemical Property:

• PSA: 100.27000
• LogP: 2.28190
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 239.09060590
• Heavy Atom Count: 17
• Complexity: 295

Purity/Quality:

98%Min ^*data from raw suppliers

4-(N-Boc-amino)-3-nitropyridine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=C(C=NC=C1)[N+](=O)[O-]

Technology Process of tert-Butyl (3-nitropyridin-4-yl)carbamate

There total 2 articles about tert-Butyl (3-nitropyridin-4-yl)carbamate 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: 51.0%

N-(4-pyridyl) t-butyl carbamate (98400-69-2) → (3-nitro-pyridin-4-yl)-carbamic acid tert-butyl ester (623562-22-1)

Guidance literature:

N-(4-pyridyl) t-butyl carbamate; With dinitrogen pentoxide; In nitromethane; cooling;

With sodium hydrogensulfite; In methanol; at 20 ℃;

DOI:10.1002/jhet.5570400405

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 4-amino-3-nitropyridine (1681-37-4) → (3-nitro-pyridin-4-yl)-carbamic acid tert-butyl ester (623562-22-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 48h;

Reference yield:

(3-nitro-pyridin-4-yl)-carbamic acid tert-butyl ester (623562-22-1) → 1-(2-chloro-phenyl)-4-methyl-2,3,5,7,9b-pentaazacyclopenta[a]naphthalene (1426833-07-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: palladium 10% on activated carbon; hydrogen / ethanol / 48 h / 50 °C / 2585.81 Torr

2.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C

3.1: dihydrogen peroxide; sodium hydroxide / water / 96 h / 75 °C / pH 7-8

4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

5.1: hydrazine hydrate / ethanol / 0.33 h / 85 °C

6.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

7.1: P,P-dichlorophenylphosphine oxide; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.67 h / 0 - 20 °C

7.2: 1 h / 20 °C

With P,P-dichlorophenylphosphine oxide; hydrogenchloride; palladium 10% on activated carbon; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; dihydrogen peroxide; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

N-(4-pyridyl) t-butyl carbamate

di-tert-butyl dicarbonate

4-amino-3-nitropyridine

Downstream raw materials:

1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one

t-butyl 6-N-butylamin-3-aminopyridin-4-yl carbamate

1-(2-chloro-phenyl)-4-methyl-2,3,5,7,9b-pentaazacyclopenta[a]naphthalene

C₁₅H₁₂ClN₅O

Refernces

• 1、 Bakke, Jan M.,Gautun, Hanna S. H.,Svensen, Harald. "Preparation of substituted 1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-ones". . p. 585 - 591. Retrieved 2007/10/03.