5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC ACID

Base Information

• Chemical Name: 5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC ACID
• CAS No.: 58483-95-7
• Molecular Formula: C6H5 Cl N2 O2
• Molecular Weight: 172.571
• Hs Code.: 2933399090
• Mol file: 58483-95-7.mol

Synonyms:3-amino-6-chloroisonicotinicacid; 5-Amino-2-chloroisonicotinic acid; 5-Amino-2-chloropyridine-4-carboxylicacid

Chemical Property of 5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 514.41oC at 760 mmHg
• PKA: 3.74±0.10(Predicted)
• Flash Point: 264.906oC
• PSA: 76.21000
• Density: 1.577g/cm3
• LogP: 1.59660
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

99% ^*data from raw suppliers

3-Amino-6-chloroisonicotinicAcid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Amino-6-chloroisonicotinic Acid is a useful synthetic intermediate. It can be used to prepare inhibitors of the EGFr and c-erbB-2. It can also be used to synthesise modulators of GHSr-1a for the treatment of type II diabetes and obesity.

Technology Process of 5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC ACID

There total 6 articles about 5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC 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: 87.0%

5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid (171178-46-4) → 5‐amino‐2‐chloropyridine‐4‐carboxylic acid (58483-95-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1039/p19960002221

Reference yield:

tert-butyl (6-chloropyridin-3-yl)carbamate (171178-45-3) → 5‐amino‐2‐chloropyridine‐4‐carboxylic acid (58483-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi; TMEDA / toluene / -60 - -15 °C

1.2: 65 percent / toluene

2.1: 85 percent / aq. NaOH

With sodium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In toluene;

DOI:10.1016/S0960-894X(01)00219-0

Reference yield:

6-Chloro-pyridin-3-ylamine (5350-93-6) → 5‐amino‐2‐chloropyridine‐4‐carboxylic acid (58483-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / dioxane / 12 h / Heating

2: 57 percent / TMEDA, BuLi / diethyl ether; hexane / 1.) -10 deg C, 2 h, 2.) -78 deg C to 20 deg C

3: 87 percent / TFA / CH₂Cl₂

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; trifluoroacetic acid; In 1,4-dioxane; diethyl ether; hexane; dichloromethane;

DOI:10.1039/p19960002221

upstream raw materials:

5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid

6-Chloro-3-pyridinecarboxylic acid

tert-butyl (6-chloropyridin-3-yl)carbamate

6-Chloro-pyridin-3-ylamine

Downstream raw materials:

4,6-dichloro-pyrido<3,4-d>pyrimidine

4-chloro-6-(N,N-dimethylamino)-pyrido[3,4-d]pyrimidine

6-dimethylamino-3H-pyrido[3,4-d]pyrimidin-4-one

(1-benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amine

Refernces

• 1、 -. "HETEROCYCLIC HYDRAZIDE COMPOUND AND PESTICIDAL USE OF THE SAME". Page/Page column 405-406. . Retrieved 2008/12/08.
• 2、 -. "PYRIDO [3,4-D] PYRIMIDINE DERIVATIVES AS MATRIX METALLOPROTEINASE-13 INHIBITORS". Page/Page column 115-116; 123. . Retrieved 2010/02/11.