2-AMINO-5-CHLORO-NICOTINIC ACID METHYL ESTER
- Product Name
- 2-AMINO-5-CHLORO-NICOTINIC ACID METHYL ESTER
- CAS No.
- 50735-33-6
- Chemical Name
- 2-AMINO-5-CHLORO-NICOTINIC ACID METHYL ESTER
- Synonyms
- methyl 2-amino-5-chloronicotinate;2-AMINO-5-CHLORO-NICOTINIC ACID METHYL ESTER;Methyl 2-aMino-5-chloropyridine-3-carboxylate;3-Pyridinecarboxylic acid, 2-amino-5-chloro-, methyl ester
- CBNumber
- CB4845603
- Molecular Formula
- C7H7ClN2O2
- Formula Weight
- 186.6
- MOL File
- 50735-33-6.mol
2-AMINO-5-CHLORO-NICOTINIC ACID METHYL ESTER Property
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- Appearance
- Light yellow to brown Solid
- InChI
- InChI=1S/C7H7ClN2O2/c1-12-7(11)5-2-4(8)3-10-6(5)9/h2-3H,1H3,(H2,9,10)
- InChIKey
- PEYKGXOKTQNWCI-UHFFFAOYSA-N
- SMILES
- C1(N)=NC=C(Cl)C=C1C(OC)=O
Safety
- HS Code
- 2933399990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- M328630
- Product name
- Methyl2-amino-5-chloropyridine-3-carboxylate
- Packaging
- 100mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- M328630
- Product name
- Methyl2-amino-5-chloropyridine-3-carboxylate
- Packaging
- 500mg
- Price
- $65
- Updated
- 2021/12/16
- Product number
- 4H58-5-C6
- Product name
- Methyl 2-amino-5-chloronicotinate
- Packaging
- 1g
- Price
- $160
- Updated
- 2021/12/16
- Product number
- 7006AB
- Product name
- Methyl2-amino-5-chloronicotinate
- Packaging
- 10g
- Price
- $200
- Updated
- 2021/12/16
- Product number
- 088196
- Product name
- Methyl 2-amino-5-chloronicotinate
- Packaging
- 1g
- Price
- $269
- Updated
- 2021/12/16
2-AMINO-5-CHLORO-NICOTINIC ACID METHYL ESTER Chemical Properties,Usage,Production
Synthesis
67754-03-4
50735-33-6
The general procedure for the synthesis of 2-amino-5-chloronicotinic acid methyl ester from 2,5-dichloronicotinic acid was as follows: first, 2,5-dichloronicotinic acid (20.2 g, 0.105 mol) was dissolved in methanol (500 mL) and cooled to 0 °C. Subsequently, pure thionyl chloride (38 mL, 63 g, 0.525 mol) was slowly added and the reaction temperature was kept at 0 °C with stirring for 1 hour. After that, the cooling bath was removed and the reaction mixture was allowed to warm up to room temperature and stirring was continued for 2 days. After completion of the reaction, the solvent was removed by distillation under reduced pressure to give an off-white residue. The residue was dissolved in ether (~500 mL) and washed sequentially with saturated aqueous NaHCO3 solution (~300 mL), water (~300 mL) and brine (~300 mL). The organic layer was separated, dried with anhydrous MgSO4 and filtered. The solvent was again removed by distillation under reduced pressure to afford methyl 2,5-dichloronicotinate (21.0 g, 97% yield) as a white solid. Next, the reaction was carried out in parallel in two pressure vessels by dissolving methyl 2,5-dichloronicotinate (4.5 g, 22 mmol) in an ammonia solution (250 mL, 0.5 M; 0.125 mol) in 1,4-dioxane. The pressure vessel was sealed and heated at 85±5°C for 9 days. After completion of the reaction, it was cooled to room temperature, the reaction mixture was combined and concentrated under reduced pressure to give a white solid. The solid was dissolved in a 1:1 acetone-methanol solvent mixture (about 500 mL), adsorbed onto silica gel (25 g) and purified by fast column chromatography (25:10:1 hexane-dichloromethane-ether solvent mixture) to afford methyl 2-amino-5-chloronicotinate (6.08 g, 75% yield). Finally, a solution of LiOH-H2O (1.38 g, 33 mmol) in water (33 mL) was added at once to a methanol (110 mL) suspension of methyl 2-amino-5-chloronicotinate (6.08 g, 27 mmol). The reaction mixture was stirred at 70 °C for 24 h. The reaction mixture gradually became homogeneous. After removing the solvent under reduced pressure, the resulting white solid was dried under vacuum (<1 mmHg) to constant weight to afford lithium 2-amino-5-chloronicotinate (5.51 g, 95% yield).
References
[1] Patent: WO2006/88840, 2006, A1. Location in patent: Page/Page column 126-127
[2] Patent: WO2006/91428, 2006, A2. Location in patent: Page/Page column 124
[3] Patent: WO2006/88837, 2006, A2. Location in patent: Page/Page column 120
[4] Patent: WO2007/109238, 2007, A1. Location in patent: Page/Page column 99-100
2-AMINO-5-CHLORO-NICOTINIC ACID METHYL ESTER Preparation Products And Raw materials
Raw materials
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