N2-METHYL-PYRIDINE-2,3-DIAMINE

N2-METHYL-PYRIDINE-2,3-DIAMINE Property

Melting point:

100-101 °C

Boiling point:

145 °C

Density 

1.179±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

7.04±0.10(Predicted)

Appearance

Brown to purple Solid

Safety

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

N2-METHYL-PYRIDINE-2,3-DIAMINE Chemical Properties,Usage,Production

Uses

N2-Methylpyridine-2,3-diamine is a useful reagent in synthesis of imidazopyridines, which show tuberculostatic activity.

Synthesis

General procedure for the synthesis of N2-methyl-2,3-pyridinediamine from N-methyl-3-nitropyridin-2-amine: N-methyl-3-nitropyridin-2-amine (58.14 g, 0.38 mol) was dissolved in 1,2-dimethoxyethane (400 mL) under vigorous stirring. Activated carbon (2.9 g) was added to the resulting solution, refluxed for 2 hours and left at room temperature overnight. After displacing the reaction system with dry nitrogen, 10% Pd/C catalyst (1.75 g) was added. The mixture was heated to 40 °C and hydrazine monohydrate (54 mL, 1.08 mol) was slowly added dropwise over a period of 2 hours. After dropwise addition, the reaction mixture was refluxed for 2 h. After cooling, the reaction mixture was filtered through a column of diatomaceous earth (upper layer, 3 cm) and silica gel (lower layer, 5 cm, 13 cm diameter) to remove the catalyst. The filtrate layer was washed with 1,2-dimethoxyethane (300 mL). The filtrate was concentrated under reduced pressure to afford N2-methyl-2,3-pyridinediamine in 98% yield (46.2 g) as a brown crystalline solid. The product could be used directly in the subsequent reaction without further purification.

References

[1] Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14173 - 14176
[2] Open Medicinal Chemistry Journal, 2018, vol. 12, # 1, p. 74 - 83
[3] Patent: WO2008/12622, 2008, A2. Location in patent: Page/Page column 57
[4] Patent: CN106831776, 2017, A. Location in patent: Paragraph 0100; 0101; 0102
[5] Patent: WO2012/121936, 2012, A2. Location in patent: Page/Page column 93-94